# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_8f
_database_code_depnum_ccdc_archive 'CCDC 2089290'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H21 N O6'
_chemical_formula_sum            'C16 H21 N O6'
_chemical_formula_weight         323.34

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'
N N 0.0061 0.0033 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   8.1315(6)
_cell_length_b                   13.2200(10)
_cell_length_c                   14.3234(9)
_cell_angle_alpha                84.858(3)
_cell_angle_beta                 89.157(3)
_cell_angle_gamma                89.327(3)
_cell_volume                     1533.30(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2495
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      20.89

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       '/f and /w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23542
_diffrn_reflns_av_unetI/netI     0.0822
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.774
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6992
_reflns_number_gt                3809
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0561P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6992
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1409
_refine_ls_wR_factor_gt          0.1171
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1795(2) 0.62253(13) 0.54717(13) 0.0638(6) Uani 1 1 d . . . . .
O2 O -0.0669(2) 0.69172(13) 0.52003(12) 0.0535(5) Uani 1 1 d . . . . .
O3 O 0.3045(2) 0.59885(13) 0.36958(13) 0.0613(5) Uani 1 1 d . . . . .
O4 O 0.5495(2) 0.67081(12) 0.37235(12) 0.0516(5) Uani 1 1 d . . . . .
O10 O 0.31162(19) 0.92823(11) 0.46274(10) 0.0388(4) Uani 1 1 d . . . . .
O11 O 0.12929(19) 0.89724(11) 0.31967(10) 0.0416(4) Uani 1 1 d . . . . .
N2 N 0.4894(3) 0.95594(17) 0.28877(15) 0.0481(6) Uani 1 1 d . . . . .
H2 H 0.429(3) 1.001(2) 0.3041(19) 0.061(10) Uiso 1 1 d . . . . .
C1 C 0.5570(3) 0.90363(18) 0.37394(17) 0.0455(6) Uani 1 1 d . . . . .
H1A H 0.614635 0.952453 0.407769 0.055 Uiso 1 1 calc R U . . .
H1B H 0.636802 0.853285 0.356534 0.055 Uiso 1 1 calc R U . . .
C3 C 0.3924(3) 0.88733(19) 0.23758(16) 0.0467(6) Uani 1 1 d . . . . .
H3A H 0.466855 0.838561 0.212208 0.056 Uiso 1 1 calc R U . . .
H3B H 0.342134 0.926751 0.184924 0.056 Uiso 1 1 calc R U . . .
C3A C 0.2585(3) 0.82934(17) 0.29273(15) 0.0371(6) Uani 1 1 d . . . . .
C4 C 0.1562(3) 0.7566(2) 0.24051(17) 0.0514(7) Uani 1 1 d . . . . .
H4A H 0.213461 0.692486 0.235425 0.062 Uiso 1 1 calc R U . . .
H4B H 0.127663 0.786224 0.178381 0.062 Uiso 1 1 calc R U . . .
C5 C 0.0036(3) 0.7434(2) 0.30490(18) 0.0529(7) Uani 1 1 d . . . . .
H5A H -0.096858 0.757812 0.270317 0.063 Uiso 1 1 calc R U . . .
H5B H -0.001275 0.675347 0.336290 0.063 Uiso 1 1 calc R U . . .
C6 C 0.0330(3) 0.82271(17) 0.37473(16) 0.0408(6) Uani 1 1 d . . . . .
H6A H -0.068665 0.850374 0.400389 0.049 Uiso 1 1 calc R U . . .
C6A C 0.1553(3) 0.78151(16) 0.45050(15) 0.0337(5) Uani 1 1 d . . . . .
C7 C 0.2047(3) 0.86260(17) 0.51862(15) 0.0387(6) Uani 1 1 d . . . . .
H7A H 0.109797 0.898131 0.543809 0.046 Uiso 1 1 calc R U . . .
C8 C 0.3232(3) 0.8188(2) 0.59487(16) 0.0510(7) Uani 1 1 d . . . . .
H8A H 0.285072 0.754406 0.624770 0.061 Uiso 1 1 calc R U . . .
H8B H 0.339411 0.865747 0.642122 0.061 Uiso 1 1 calc R U . . .
C9 C 0.4813(3) 0.8053(2) 0.53559(16) 0.0500(7) Uani 1 1 d . . . . .
H9A H 0.572732 0.841677 0.559021 0.060 Uiso 1 1 calc R U . . .
H9B H 0.511274 0.734214 0.534589 0.060 Uiso 1 1 calc R U . . .
C9A C 0.4295(3) 0.85177(17) 0.43833(15) 0.0349(5) Uani 1 1 d . . . . .
C9B C 0.3177(3) 0.77759(16) 0.39044(14) 0.0323(5) Uani 1 1 d . . . . .
C10 C 0.0958(3) 0.68770(18) 0.50862(16) 0.0408(6) Uani 1 1 d . . . . .
C11 C -0.1396(4) 0.6095(2) 0.5802(2) 0.0712(9) Uani 1 1 d . . . . .
H11A H -0.256570 0.619602 0.583668 0.107 Uiso 1 1 calc R U . . .
H11B H -0.115836 0.546054 0.554824 0.107 Uiso 1 1 calc R U . . .
H11C H -0.094525 0.608461 0.641826 0.107 Uiso 1 1 calc R U . . .
C12 C 0.3860(3) 0.67218(18) 0.37866(16) 0.0395(6) Uani 1 1 d . . . . .
C13 C 0.6229(4) 0.5726(2) 0.3587(2) 0.0677(9) Uani 1 1 d . . . . .
H13A H 0.740354 0.578705 0.354919 0.102 Uiso 1 1 calc R U . . .
H13B H 0.593482 0.524807 0.410474 0.102 Uiso 1 1 calc R U . . .
H13C H 0.583324 0.549402 0.301579 0.102 Uiso 1 1 calc R U . . .
O21 O 0.7403(2) 0.92626(12) 0.95050(11) 0.0538(5) Uani 1 1 d . . . . .
O22 O 0.8084(2) 0.85560(12) 1.09212(11) 0.0521(5) Uani 1 1 d . . . . .
O23 O 0.6544(2) 0.78034(15) 0.73453(11) 0.0611(5) Uani 1 1 d . . . . .
O24 O 0.8750(2) 0.81343(12) 0.81450(10) 0.0439(4) Uani 1 1 d . . . . .
O30 O 0.44747(18) 0.65391(11) 0.98886(9) 0.0354(4) Uani 1 1 d . . . . .
O31 O 0.74247(18) 0.57291(10) 1.00382(10) 0.0362(4) Uani 1 1 d . . . . .
N22 N 0.5176(3) 0.51414(15) 0.85027(15) 0.0400(5) Uani 1 1 d . . . . .
H22 H 0.489(3) 0.486(2) 0.9078(19) 0.070(9) Uiso 1 1 d . . . . .
C21 C 0.4297(3) 0.60992(17) 0.83087(16) 0.0403(6) Uani 1 1 d . . . . .
H21A H 0.312723 0.598209 0.839676 0.048 Uiso 1 1 calc R U . . .
H21B H 0.448384 0.634517 0.765768 0.048 Uiso 1 1 calc R U . . .
C23 C 0.6949(3) 0.52613(17) 0.84617(16) 0.0390(6) Uani 1 1 d . . . . .
H23A H 0.727059 0.544355 0.781414 0.047 Uiso 1 1 calc R U . . .
H23B H 0.745453 0.460806 0.865084 0.047 Uiso 1 1 calc R U . . .
C23A C 0.7645(3) 0.60339(16) 0.90507(15) 0.0328(5) Uani 1 1 d . . . . .
C24 C 0.9510(3) 0.61742(18) 0.90213(17) 0.0437(6) Uani 1 1 d . . . . .
H24A H 0.985667 0.659727 0.846671 0.052 Uiso 1 1 calc R U . . .
H24B H 1.008757 0.552674 0.904061 0.052 Uiso 1 1 calc R U . . .
C25 C 0.9783(3) 0.67044(18) 0.99198(17) 0.0468(7) Uani 1 1 d . . . . .
H25A H 1.060888 0.635266 1.031247 0.056 Uiso 1 1 calc R U . . .
H25B H 1.010134 0.740666 0.977674 0.056 Uiso 1 1 calc R U . . .
C26 C 0.8065(3) 0.66249(16) 1.03833(16) 0.0377(6) Uani 1 1 d . . . . .
H26A H 0.808874 0.659299 1.106920 0.045 Uiso 1 1 calc R U . . .
C26A C 0.6919(3) 0.74703(15) 0.99404(14) 0.0317(5) Uani 1 1 d . . . . .
C27 C 0.5105(3) 0.73876(17) 1.03125(15) 0.0386(6) Uani 1 1 d . . . . .
H27A H 0.502409 0.730983 1.099845 0.046 Uiso 1 1 calc R U . . .
C28 C 0.4017(3) 0.82470(18) 0.98714(16) 0.0452(6) Uani 1 1 d . . . . .
H28A H 0.454034 0.890186 0.987749 0.054 Uiso 1 1 calc R U . . .
H28B H 0.295346 0.826691 1.018546 0.054 Uiso 1 1 calc R U . . .
C29A C 0.4810(3) 0.69095(16) 0.89252(14) 0.0325(5) Uani 1 1 d . . . . .
C29B C 0.6691(3) 0.70936(15) 0.89362(14) 0.0280(5) Uani 1 1 d . . . . .
C29 C 0.3864(3) 0.79302(18) 0.88609(16) 0.0424(6) Uani 1 1 d . . . . .
H29A H 0.272348 0.784491 0.869793 0.051 Uiso 1 1 calc R U . . .
H29B H 0.437038 0.842298 0.840593 0.051 Uiso 1 1 calc R U . . .
C30 C 0.7514(3) 0.85286(17) 1.00486(16) 0.0366(6) Uani 1 1 d . . . . .
C31 C 0.8522(4) 0.95423(19) 1.12082(19) 0.0661(9) Uani 1 1 d . . . . .
H31A H 0.891075 0.946491 1.184055 0.099 Uiso 1 1 calc R U . . .
H31B H 0.937300 0.983213 1.079972 0.099 Uiso 1 1 calc R U . . .
H31C H 0.757332 0.998213 1.117409 0.099 Uiso 1 1 calc R U . . .
C32 C 0.7287(3) 0.77234(16) 0.80677(16) 0.0357(5) Uani 1 1 d . . . . .
C33 C 0.9456(3) 0.8637(2) 0.73052(18) 0.0575(7) Uani 1 1 d . . . . .
H33A H 1.050886 0.890431 0.744205 0.086 Uiso 1 1 calc R U . . .
H33B H 0.958767 0.815999 0.684138 0.086 Uiso 1 1 calc R U . . .
H33C H 0.874156 0.918188 0.707089 0.086 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.193(3) . ?
O2 C10 1.332(3) . ?
O2 C11 1.451(3) . ?
O3 C12 1.198(3) . ?
O4 C12 1.331(3) . ?
O4 C13 1.450(3) . ?
O10 C7 1.422(3) . ?
O10 C9A 1.447(3) . ?
O11 C6 1.438(3) . ?
O11 C3A 1.444(3) . ?
N2 C1 1.459(3) . ?
N2 C3 1.462(3) . ?
N2 H2 0.81(3) . ?
C1 C9A 1.507(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 C3A 1.511(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3A C4 1.530(3) . ?
C3A C9B 1.581(3) . ?
C4 C5 1.537(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.535(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C6A 1.542(3) . ?
C6 H6A 0.9800 . ?
C6A C10 1.511(3) . ?
C6A C9B 1.568(3) . ?
C6A C7 1.572(3) . ?
C7 C8 1.537(3) . ?
C7 H7A 0.9800 . ?
C8 C9 1.547(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C9A 1.534(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9A C9B 1.555(3) . ?
C9B C12 1.517(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O21 C30 1.192(3) . ?
O22 C30 1.343(3) . ?
O22 C31 1.452(3) . ?
O23 C32 1.201(2) . ?
O24 C32 1.324(3) . ?
O24 C33 1.436(3) . ?
O30 C27 1.426(2) . ?
O30 C29A 1.445(2) . ?
O31 C26 1.430(2) . ?
O31 C23A 1.445(2) . ?
N22 C23 1.452(3) . ?
N22 C21 1.454(3) . ?
N22 H22 0.90(3) . ?
C21 C29A 1.514(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C23 C23A 1.503(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23A C24 1.529(3) . ?
C23A C29B 1.590(3) . ?
C24 C25 1.540(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.539(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C26A 1.545(3) . ?
C26 H26A 0.9800 . ?
C26A C30 1.508(3) . ?
C26A C27 1.562(3) . ?
C26A C29B 1.578(3) . ?
C27 C28 1.529(3) . ?
C27 H27A 0.9800 . ?
C28 C29 1.550(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29A C29 1.542(3) . ?
C29A C29B 1.552(3) . ?
C29B C32 1.511(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?

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
C10 O2 C11 116.1(2) . . ?
C12 O4 C13 115.1(2) . . ?
C7 O10 C9A 97.41(16) . . ?
C6 O11 C3A 97.16(16) . . ?
C1 N2 C3 111.29(19) . . ?
C1 N2 H2 107.8(19) . . ?
C3 N2 H2 108(2) . . ?
N2 C1 C9A 113.9(2) . . ?
N2 C1 H1A 108.8 . . ?
C9A C1 H1A 108.8 . . ?
N2 C1 H1B 108.8 . . ?
C9A C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
N2 C3 C3A 116.42(19) . . ?
N2 C3 H3A 108.2 . . ?
C3A C3 H3A 108.2 . . ?
N2 C3 H3B 108.2 . . ?
C3A C3 H3B 108.2 . . ?
H3A C3 H3B 107.3 . . ?
O11 C3A C3 110.86(18) . . ?
O11 C3A C4 99.43(18) . . ?
C3 C3A C4 117.20(19) . . ?
O11 C3A C9B 102.56(16) . . ?
C3 C3A C9B 113.40(19) . . ?
C4 C3A C9B 111.46(19) . . ?
C3A C4 C5 101.27(19) . . ?
C3A C4 H4A 111.5 . . ?
C5 C4 H4A 111.5 . . ?
C3A C4 H4B 111.5 . . ?
C5 C4 H4B 111.5 . . ?
H4A C4 H4B 109.3 . . ?
C6 C5 C4 101.82(19) . . ?
C6 C5 H5A 111.4 . . ?
C4 C5 H5A 111.4 . . ?
C6 C5 H5B 111.4 . . ?
C4 C5 H5B 111.4 . . ?
H5A C5 H5B 109.3 . . ?
O11 C6 C5 102.20(19) . . ?
O11 C6 C6A 102.29(17) . . ?
C5 C6 C6A 110.63(19) . . ?
O11 C6 H6A 113.5 . . ?
C5 C6 H6A 113.5 . . ?
C6A C6 H6A 113.5 . . ?
C10 C6A C6 113.49(19) . . ?
C10 C6A C9B 120.33(18) . . ?
C6 C6A C9B 100.59(17) . . ?
C10 C6A C7 108.51(18) . . ?
C6 C6A C7 113.38(18) . . ?
C9B C6A C7 99.85(17) . . ?
O10 C7 C8 100.71(19) . . ?
O10 C7 C6A 103.45(16) . . ?
C8 C7 C6A 112.27(18) . . ?
O10 C7 H7A 113.1 . . ?
C8 C7 H7A 113.1 . . ?
C6A C7 H7A 113.1 . . ?
C7 C8 C9 100.63(18) . . ?
C7 C8 H8A 111.6 . . ?
C9 C8 H8A 111.6 . . ?
C7 C8 H8B 111.6 . . ?
C9 C8 H8B 111.6 . . ?
H8A C8 H8B 109.4 . . ?
C9A C9 C8 102.10(18) . . ?
C9A C9 H9A 111.3 . . ?
C8 C9 H9A 111.3 . . ?
C9A C9 H9B 111.3 . . ?
C8 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
O10 C9A C1 107.69(18) . . ?
O10 C9A C9 101.31(17) . . ?
C1 C9A C9 119.0(2) . . ?
O10 C9A C9B 101.45(16) . . ?
C1 C9A C9B 114.21(18) . . ?
C9 C9A C9B 110.68(19) . . ?
C12 C9B C9A 117.32(18) . . ?
C12 C9B C6A 115.57(19) . . ?
C9A C9B C6A 101.77(16) . . ?
C12 C9B C3A 109.96(17) . . ?
C9A C9B C3A 109.72(17) . . ?
C6A C9B C3A 101.08(17) . . ?
O1 C10 O2 122.9(2) . . ?
O1 C10 C6A 126.5(2) . . ?
O2 C10 C6A 110.3(2) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 O4 122.6(2) . . ?
O3 C12 C9B 125.0(2) . . ?
O4 C12 C9B 112.3(2) . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C30 O22 C31 117.16(18) . . ?
C32 O24 C33 116.58(19) . . ?
C27 O30 C29A 97.31(16) . . ?
C26 O31 C23A 97.38(15) . . ?
C23 N22 C21 112.56(19) . . ?
C23 N22 H22 108.6(18) . . ?
C21 N22 H22 109.3(17) . . ?
N22 C21 C29A 113.34(17) . . ?
N22 C21 H21A 108.9 . . ?
C29A C21 H21A 108.9 . . ?
N22 C21 H21B 108.9 . . ?
C29A C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
N22 C23 C23A 116.42(18) . . ?
N22 C23 H23A 108.2 . . ?
C23A C23 H23A 108.2 . . ?
N22 C23 H23B 108.2 . . ?
C23A C23 H23B 108.2 . . ?
H23A C23 H23B 107.3 . . ?
O31 C23A C23 111.16(18) . . ?
O31 C23A C24 99.31(16) . . ?
C23 C23A C24 117.48(19) . . ?
O31 C23A C29B 102.28(15) . . ?
C23 C23A C29B 112.98(17) . . ?
C24 C23A C29B 111.68(18) . . ?
C23A C24 C25 101.58(18) . . ?
C23A C24 H24A 111.5 . . ?
C25 C24 H24A 111.5 . . ?
C23A C24 H24B 111.5 . . ?
C25 C24 H24B 111.5 . . ?
H24A C24 H24B 109.3 . . ?
C26 C25 C24 101.30(18) . . ?
C26 C25 H25A 111.5 . . ?
C24 C25 H25A 111.5 . . ?
C26 C25 H25B 111.5 . . ?
C24 C25 H25B 111.5 . . ?
H25A C25 H25B 109.3 . . ?
O31 C26 C25 102.67(18) . . ?
O31 C26 C26A 102.80(16) . . ?
C25 C26 C26A 110.24(18) . . ?
O31 C26 H26A 113.4 . . ?
C25 C26 H26A 113.4 . . ?
C26A C26 H26A 113.4 . . ?
C30 C26A C26 113.66(18) . . ?
C30 C26A C27 108.40(18) . . ?
C26 C26A C27 113.49(18) . . ?
C30 C26A C29B 120.66(18) . . ?
C26 C26A C29B 100.34(16) . . ?
C27 C26A C29B 99.57(16) . . ?
O30 C27 C28 101.04(17) . . ?
O30 C27 C26A 103.94(16) . . ?
C28 C27 C26A 111.95(19) . . ?
O30 C27 H27A 113.0 . . ?
C28 C27 H27A 113.0 . . ?
C26A C27 H27A 113.0 . . ?
C27 C28 C29 100.89(17) . . ?
C27 C28 H28A 111.6 . . ?
C29 C28 H28A 111.6 . . ?
C27 C28 H28B 111.6 . . ?
C29 C28 H28B 111.6 . . ?
H28A C28 H28B 109.4 . . ?
O30 C29A C21 107.92(18) . . ?
O30 C29A C29 100.92(16) . . ?
C21 C29A C29 118.88(18) . . ?
O30 C29A C29B 101.93(15) . . ?
C21 C29A C29B 114.49(18) . . ?
C29 C29A C29B 110.29(18) . . ?
C32 C29B C29A 112.23(17) . . ?
C32 C29B C26A 120.83(18) . . ?
C29A C29B C26A 101.82(16) . . ?
C32 C29B C23A 110.44(17) . . ?
C29A C29B C23A 109.69(17) . . ?
C26A C29B C23A 100.86(15) . . ?
C29A C29 C28 101.82(17) . . ?
C29A C29 H29A 111.4 . . ?
C28 C29 H29A 111.4 . . ?
C29A C29 H29B 111.4 . . ?
C28 C29 H29B 111.4 . . ?
H29A C29 H29B 109.3 . . ?
O21 C30 O22 123.2(2) . . ?
O21 C30 C26A 128.0(2) . . ?
O22 C30 C26A 108.54(18) . . ?
O22 C31 H31A 109.5 . . ?
O22 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O22 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O23 C32 O24 122.1(2) . . ?
O23 C32 C29B 123.1(2) . . ?
O24 C32 C29B 114.61(18) . . ?
O24 C33 H33A 109.5 . . ?
O24 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O24 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C1 C9A -55.0(3) . . . . ?
C1 N2 C3 C3A 52.9(3) . . . . ?
C6 O11 C3A C3 -175.77(17) . . . . ?
C6 O11 C3A C4 60.23(19) . . . . ?
C6 O11 C3A C9B -54.41(18) . . . . ?
N2 C3 C3A O11 67.2(3) . . . . ?
N2 C3 C3A C4 -179.6(2) . . . . ?
N2 C3 C3A C9B -47.5(3) . . . . ?
O11 C3A C4 C5 -41.5(2) . . . . ?
C3 C3A C4 C5 -160.9(2) . . . . ?
C9B C3A C4 C5 66.1(2) . . . . ?
C3A C4 C5 C6 8.0(2) . . . . ?
C3A O11 C6 C5 -55.21(19) . . . . ?
C3A O11 C6 C6A 59.38(19) . . . . ?
C4 C5 C6 O11 28.2(2) . . . . ?
C4 C5 C6 C6A -80.1(2) . . . . ?
O11 C6 C6A C10 -169.56(18) . . . . ?
C5 C6 C6A C10 -61.3(3) . . . . ?
O11 C6 C6A C9B -39.7(2) . . . . ?
C5 C6 C6A C9B 68.6(2) . . . . ?
O11 C6 C6A C7 66.0(2) . . . . ?
C5 C6 C6A C7 174.28(19) . . . . ?
C9A O10 C7 C8 59.72(18) . . . . ?
C9A O10 C7 C6A -56.50(18) . . . . ?
C10 C6A C7 O10 159.21(18) . . . . ?
C6 C6A C7 O10 -73.7(2) . . . . ?
C9B C6A C7 O10 32.43(19) . . . . ?
C10 C6A C7 C8 51.5(3) . . . . ?
C6 C6A C7 C8 178.6(2) . . . . ?
C9B C6A C7 C8 -75.3(2) . . . . ?
O10 C7 C8 C9 -39.0(2) . . . . ?
C6A C7 C8 C9 70.4(2) . . . . ?
C7 C8 C9 C9A 4.5(2) . . . . ?
C7 O10 C9A C1 177.92(17) . . . . ?
C7 O10 C9A C9 -56.41(19) . . . . ?
C7 O10 C9A C9B 57.67(18) . . . . ?
N2 C1 C9A O10 -58.2(2) . . . . ?
N2 C1 C9A C9 -172.5(2) . . . . ?
N2 C1 C9A C9B 53.7(3) . . . . ?
C8 C9 C9A O10 30.6(2) . . . . ?
C8 C9 C9A C1 148.4(2) . . . . ?
C8 C9 C9A C9B -76.4(2) . . . . ?
O10 C9A C9B C12 -163.43(18) . . . . ?
C1 C9A C9B C12 81.0(3) . . . . ?
C9 C9A C9B C12 -56.5(3) . . . . ?
O10 C9A C9B C6A -36.27(19) . . . . ?
C1 C9A C9B C6A -151.80(18) . . . . ?
C9 C9A C9B C6A 70.6(2) . . . . ?
O10 C9A C9B C3A 70.2(2) . . . . ?
C1 C9A C9B C3A -45.4(2) . . . . ?
C9 C9A C9B C3A 177.06(19) . . . . ?
C10 C6A C9B C12 12.6(3) . . . . ?
C6 C6A C9B C12 -112.76(19) . . . . ?
C7 C6A C9B C12 130.99(18) . . . . ?
C10 C6A C9B C9A -115.6(2) . . . . ?
C6 C6A C9B C9A 118.96(17) . . . . ?
C7 C6A C9B C9A 2.71(19) . . . . ?
C10 C6A C9B C3A 131.3(2) . . . . ?
C6 C6A C9B C3A 5.88(19) . . . . ?
C7 C6A C9B C3A -110.37(17) . . . . ?
O11 C3A C9B C12 151.72(18) . . . . ?
C3 C3A C9B C12 -88.7(2) . . . . ?
C4 C3A C9B C12 46.2(3) . . . . ?
O11 C3A C9B C9A -77.8(2) . . . . ?
C3 C3A C9B C9A 41.8(2) . . . . ?
C4 C3A C9B C9A 176.64(19) . . . . ?
O11 C3A C9B C6A 29.10(19) . . . . ?
C3 C3A C9B C6A 148.70(18) . . . . ?
C4 C3A C9B C6A -76.4(2) . . . . ?
C11 O2 C10 O1 -2.1(3) . . . . ?
C11 O2 C10 C6A -175.8(2) . . . . ?
C6 C6A C10 O1 152.6(2) . . . . ?
C9B C6A C10 O1 33.5(3) . . . . ?
C7 C6A C10 O1 -80.4(3) . . . . ?
C6 C6A C10 O2 -34.0(3) . . . . ?
C9B C6A C10 O2 -153.10(18) . . . . ?
C7 C6A C10 O2 93.0(2) . . . . ?
C13 O4 C12 O3 -3.2(3) . . . . ?
C13 O4 C12 C9B -178.57(19) . . . . ?
C9A C9B C12 O3 157.1(2) . . . . ?
C6A C9B C12 O3 36.9(3) . . . . ?
C3A C9B C12 O3 -76.7(3) . . . . ?
C9A C9B C12 O4 -27.7(3) . . . . ?
C6A C9B C12 O4 -147.81(19) . . . . ?
C3A C9B C12 O4 98.6(2) . . . . ?
C23 N22 C21 C29A -53.9(3) . . . . ?
C21 N22 C23 C23A 53.0(3) . . . . ?
C26 O31 C23A C23 -175.60(18) . . . . ?
C26 O31 C23A C24 60.00(17) . . . . ?
C26 O31 C23A C29B -54.76(18) . . . . ?
N22 C23 C23A O31 66.5(2) . . . . ?
N22 C23 C23A C24 179.92(19) . . . . ?
N22 C23 C23A C29B -47.8(3) . . . . ?
O31 C23A C24 C25 -41.5(2) . . . . ?
C23 C23A C24 C25 -161.32(19) . . . . ?
C29B C23A C24 C25 65.8(2) . . . . ?
C23A C24 C25 C26 8.4(2) . . . . ?
C23A O31 C26 C25 -55.00(17) . . . . ?
C23A O31 C26 C26A 59.51(19) . . . . ?
C24 C25 C26 O31 27.8(2) . . . . ?
C24 C25 C26 C26A -81.2(2) . . . . ?
O31 C26 C26A C30 -169.33(18) . . . . ?
C25 C26 C26A C30 -60.4(2) . . . . ?
O31 C26 C26A C27 66.2(2) . . . . ?
C25 C26 C26A C27 175.06(17) . . . . ?
O31 C26 C26A C29B -39.1(2) . . . . ?
C25 C26 C26A C29B 69.8(2) . . . . ?
C29A O30 C27 C28 59.67(19) . . . . ?
C29A O30 C27 C26A -56.49(18) . . . . ?
C30 C26A C27 O30 159.93(16) . . . . ?
C26 C26A C27 O30 -72.8(2) . . . . ?
C29B C26A C27 O30 32.98(19) . . . . ?
C30 C26A C27 C28 51.7(2) . . . . ?
C26 C26A C27 C28 178.99(17) . . . . ?
C29B C26A C27 C28 -75.2(2) . . . . ?
O30 C27 C28 C29 -38.1(2) . . . . ?
C26A C27 C28 C29 72.0(2) . . . . ?
C27 O30 C29A C21 177.73(18) . . . . ?
C27 O30 C29A C29 -56.86(18) . . . . ?
C27 O30 C29A C29B 56.83(17) . . . . ?
N22 C21 C29A O30 -60.3(2) . . . . ?
N22 C21 C29A C29 -174.3(2) . . . . ?
N22 C21 C29A C29B 52.4(3) . . . . ?
O30 C29A C29B C32 -166.01(16) . . . . ?
C21 C29A C29B C32 77.8(2) . . . . ?
C29 C29A C29B C32 -59.5(2) . . . . ?
O30 C29A C29B C26A -35.38(18) . . . . ?
C21 C29A C29B C26A -151.59(18) . . . . ?
C29 C29A C29B C26A 71.16(19) . . . . ?
O30 C29A C29B C23A 70.84(18) . . . . ?
C21 C29A C29B C23A -45.4(2) . . . . ?
C29 C29A C29B C23A 177.37(16) . . . . ?
C30 C26A C29B C32 8.7(3) . . . . ?
C26 C26A C29B C32 -116.9(2) . . . . ?
C27 C26A C29B C32 126.9(2) . . . . ?
C30 C26A C29B C29A -116.4(2) . . . . ?
C26 C26A C29B C29A 118.02(18) . . . . ?
C27 C26A C29B C29A 1.81(19) . . . . ?
C30 C26A C29B C23A 130.6(2) . . . . ?
C26 C26A C29B C23A 5.0(2) . . . . ?
C27 C26A C29B C23A -111.18(17) . . . . ?
O31 C23A C29B C32 158.58(17) . . . . ?
C23 C23A C29B C32 -81.8(2) . . . . ?
C24 C23A C29B C32 53.2(2) . . . . ?
O31 C23A C29B C29A -77.21(18) . . . . ?
C23 C23A C29B C29A 42.4(2) . . . . ?
C24 C23A C29B C29A 177.44(17) . . . . ?
O31 C23A C29B C26A 29.65(19) . . . . ?
C23 C23A C29B C26A 149.23(19) . . . . ?
C24 C23A C29B C26A -75.7(2) . . . . ?
O30 C29A C29 C28 31.9(2) . . . . ?
C21 C29A C29 C28 149.5(2) . . . . ?
C29B C29A C29 C28 -75.3(2) . . . . ?
C27 C28 C29 C29A 3.3(2) . . . . ?
C31 O22 C30 O21 2.2(4) . . . . ?
C31 O22 C30 C26A -172.3(2) . . . . ?
C26 C26A C30 O21 144.0(2) . . . . ?
C27 C26A C30 O21 -88.8(3) . . . . ?
C29B C26A C30 O21 24.8(4) . . . . ?
C26 C26A C30 O22 -41.9(3) . . . . ?
C27 C26A C30 O22 85.3(2) . . . . ?
C29B C26A C30 O22 -161.04(19) . . . . ?
C33 O24 C32 O23 -3.3(3) . . . . ?
C33 O24 C32 C29B 172.74(18) . . . . ?
C29A C29B C32 O23 -21.5(3) . . . . ?
C26A C29B C32 O23 -141.6(2) . . . . ?
C23A C29B C32 O23 101.3(2) . . . . ?
C29A C29B C32 O24 162.49(18) . . . . ?
C26A C29B C32 O24 42.4(3) . . . . ?
C23A C29B C32 O24 -74.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1B O4 0.97 2.51 3.081(3) 117 . yes
C4 H4A O3 0.97 2.32 2.922(3) 120 . yes
C8 H8A O1 0.97 2.33 2.996(3) 125 . yes
C13 H13C N22 0.96 2.55 3.511(3) 179 2_666 yes
N22 H22 O30 0.90(3) 2.32(3) 3.068(3) 140(2) 2_667 yes
N22 H22 O31 0.90(3) 2.35(3) 3.108(3) 141(2) 2_667 yes
C24 H24A O24 0.97 2.23 2.841(3) 120 . yes
C28 H28A O21 0.97 2.42 3.095(3) 126 . yes
C29 H29B O23 0.97 2.49 3.067(3) 118 . yes
C33 H33C O11 0.96 2.44 3.231(3) 140 2_676 yes

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.044



# start Validation Reply Form
_vrf_PLAT910_8f                  
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 19 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_16b
_database_code_depnum_ccdc_archive 'CCDC 2089295'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 O6 S'
_chemical_formula_sum            'C18 H20 O6 S'
_chemical_formula_weight         364.40

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.4171(2)
_cell_length_b                   10.0748(3)
_cell_length_c                   11.5034(3)
_cell_angle_alpha                65.859(2)
_cell_angle_beta                 82.877(2)
_cell_angle_gamma                81.991(2)
_cell_volume                     879.07(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3595
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      23.39

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.215
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       '/f and /w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16318
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.893
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5111
_reflns_number_gt                3136
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0760P)²+0.2582P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5111
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0600
_refine_ls_wR_factor_ref         0.1752
_refine_ls_wR_factor_gt          0.1518
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
S7 S 0.98019(9) 0.92170(10) 0.31994(7) 0.0792(3) Uani 1 1 d . . . . .
O1 O 0.59368(18) 0.7535(2) 0.54976(14) 0.0599(4) Uani 1 1 d . . . . .
O2 O 0.25246(18) 0.8331(2) 0.08076(16) 0.0656(5) Uani 1 1 d . . . . .
O3 O 0.4472(2) 0.6947(2) 0.02152(19) 0.0706(5) Uani 1 1 d . . . . .
O4 O 0.8845(2) 0.6343(2) 0.10261(17) 0.0764(6) Uani 1 1 d . . . . .
O5 O 0.7679(2) 0.78953(18) -0.07169(14) 0.0654(5) Uani 1 1 d . . . . .
O9 O 0.60552(15) 0.97147(14) 0.21442(13) 0.0434(3) Uani 1 1 d . . . . .
C2 C 0.4579(2) 0.8006(2) 0.4764(2) 0.0484(5) Uani 1 1 d . . . . .
H2A H 0.439016 0.907297 0.445536 0.058 Uiso 1 1 calc R U . . .
C2A C 0.5018(2) 0.7605(2) 0.36098(19) 0.0409(4) Uani 1 1 d . . . . .
H2AA H 0.451991 0.673989 0.370292 0.049 Uiso 1 1 calc R U . . .
C3 C 0.4726(2) 0.8886(2) 0.23180(19) 0.0437(5) Uani 1 1 d . . . . .
H3A H 0.366420 0.943771 0.227358 0.052 Uiso 1 1 calc R U . . .
C4 C 0.5153(2) 0.8277(2) 0.13042(18) 0.0429(4) Uani 1 1 d . . . . .
C5 C 0.6758(2) 0.8074(2) 0.12128(17) 0.0399(4) Uani 1 1 d . . . . .
C5A C 0.7313(2) 0.8561(2) 0.21895(17) 0.0387(4) Uani 1 1 d . . . . .
C6 C 0.8954(2) 0.9097(3) 0.1898(2) 0.0499(5) Uani 1 1 d . . . . .
H6A H 0.889310 1.005698 0.120388 0.060 Uiso 1 1 calc R U . . .
H6B H 0.968159 0.844872 0.159813 0.060 Uiso 1 1 calc R U . . .
C8 C 0.8092(3) 0.8977(3) 0.4337(2) 0.0594(6) Uani 1 1 d . . . . .
H8A H 0.840596 0.902385 0.510197 0.071 Uiso 1 1 calc R U . . .
H8B H 0.726639 0.977444 0.398320 0.071 Uiso 1 1 calc R U . . .
C8A C 0.7390(2) 0.7531(2) 0.47009(18) 0.0428(4) Uani 1 1 d . . . . .
C8B C 0.6885(2) 0.7350(2) 0.35261(17) 0.0375(4) Uani 1 1 d . . . . .
H8BA H 0.725443 0.637328 0.354965 0.045 Uiso 1 1 calc R U . . .
C10 C 0.3128(4) 0.7372(4) 0.5550(3) 0.0787(8) Uani 1 1 d . . . . .
H10A H 0.217969 0.774976 0.514109 0.094 Uiso 1 1 calc R U . . .
C11 C 0.2943(5) 0.6463(4) 0.6616(3) 0.1046(12) Uani 1 1 d . . . . .
H11A H 0.382432 0.602341 0.709915 0.126 Uiso 1 1 calc R U . . .
H11B H 0.191785 0.619696 0.695876 0.126 Uiso 1 1 calc R U . . .
C12 C 0.8517(3) 0.6267(3) 0.5460(2) 0.0551(5) Uani 1 1 d . . . . .
H12A H 0.956664 0.621443 0.510554 0.066 Uiso 1 1 calc R U . . .
C13 C 0.8174(4) 0.5232(3) 0.6568(3) 0.0771(8) Uani 1 1 d . . . . .
H13A H 0.714009 0.523575 0.696209 0.093 Uiso 1 1 calc R U . . .
H13B H 0.896227 0.449045 0.696432 0.093 Uiso 1 1 calc R U . . .
C14 C 0.3903(2) 0.7875(2) 0.07507(19) 0.0470(5) Uani 1 1 d . . . . .
C15 C 0.3327(4) 0.6616(4) -0.0439(4) 0.0954(11) Uani 1 1 d . . . . .
H15A H 0.377595 0.580699 -0.065166 0.143 Uiso 1 1 calc R U . . .
H15B H 0.308472 0.745456 -0.120747 0.143 Uiso 1 1 calc R U . . .
H15C H 0.235849 0.636788 0.010513 0.143 Uiso 1 1 calc R U . . .
C16 C 0.7869(2) 0.7324(2) 0.05167(19) 0.0457(5) Uani 1 1 d . . . . .
C17 C 0.8628(5) 0.7170(3) -0.1463(3) 0.0900(10) Uani 1 1 d . . . . .
H17A H 0.811331 0.738731 -0.222789 0.135 Uiso 1 1 calc R U . . .
H17B H 0.872317 0.613383 -0.097147 0.135 Uiso 1 1 calc R U . . .
H17C H 0.968011 0.750863 -0.168405 0.135 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S7 C6 1.790(2) . ?
S7 C8 1.793(3) . ?
O1 C2 1.416(3) . ?
O1 C8A 1.435(2) . ?
O2 C14 1.191(3) . ?
O3 C14 1.325(3) . ?
O3 C15 1.442(3) . ?
O4 C16 1.189(2) . ?
O5 C16 1.316(2) . ?
O5 C17 1.445(3) . ?
O9 C3 1.434(2) . ?
O9 C5A 1.448(2) . ?
C2 C10 1.479(3) . ?
C2 C2A 1.530(3) . ?
C2 H2A 0.9800 . ?
C2A C3 1.539(3) . ?
C2A C8B 1.554(3) . ?
C2A H2AA 0.9800 . ?
C3 C4 1.512(3) . ?
C3 H3A 0.9800 . ?
C4 C5 1.335(3) . ?
C4 C14 1.474(3) . ?
C5 C16 1.483(3) . ?
C5 C5A 1.539(3) . ?
C5A C6 1.502(3) . ?
C5A C8B 1.560(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 C8A 1.526(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8A C12 1.498(3) . ?
C8A C8B 1.551(3) . ?
C8B H8BA 0.9800 . ?
C10 C11 1.200(4) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C11 H11B 0.9300 . ?
C12 C13 1.304(4) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C13 H13B 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 S7 C8 101.14(11) . . ?
C2 O1 C8A 110.76(15) . . ?
C14 O3 C15 115.3(2) . . ?
C16 O5 C17 116.5(2) . . ?
C3 O9 C5A 96.62(13) . . ?
O1 C2 C10 110.9(2) . . ?
O1 C2 C2A 106.79(15) . . ?
C10 C2 C2A 113.9(2) . . ?
O1 C2 H2A 108.4 . . ?
C10 C2 H2A 108.4 . . ?
C2A C2 H2A 108.4 . . ?
C2 C2A C3 113.99(16) . . ?
C2 C2A C8B 104.70(16) . . ?
C3 C2A C8B 101.19(15) . . ?
C2 C2A H2AA 112.1 . . ?
C3 C2A H2AA 112.1 . . ?
C8B C2A H2AA 112.1 . . ?
O9 C3 C4 101.99(15) . . ?
O9 C3 C2A 102.04(15) . . ?
C4 C3 C2A 106.58(16) . . ?
O9 C3 H3A 114.9 . . ?
C4 C3 H3A 114.9 . . ?
C2A C3 H3A 114.9 . . ?
C5 C4 C14 132.9(2) . . ?
C5 C4 C3 105.26(17) . . ?
C14 C4 C3 121.38(18) . . ?
C4 C5 C16 130.50(19) . . ?
C4 C5 C5A 105.79(16) . . ?
C16 C5 C5A 123.01(16) . . ?
O9 C5A C6 111.83(16) . . ?
O9 C5A C5 100.17(14) . . ?
C6 C5A C5 116.12(16) . . ?
O9 C5A C8B 101.16(14) . . ?
C6 C5A C8B 119.38(16) . . ?
C5 C5A C8B 105.53(15) . . ?
C5A C6 S7 115.74(15) . . ?
C5A C6 H6A 108.3 . . ?
S7 C6 H6A 108.3 . . ?
C5A C6 H6B 108.3 . . ?
S7 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
C8A C8 S7 113.04(16) . . ?
C8A C8 H8A 109.0 . . ?
S7 C8 H8A 109.0 . . ?
C8A C8 H8B 109.0 . . ?
S7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
O1 C8A C12 107.56(17) . . ?
O1 C8A C8 107.87(17) . . ?
C12 C8A C8 111.02(19) . . ?
O1 C8A C8B 105.71(15) . . ?
C12 C8A C8B 111.88(16) . . ?
C8 C8A C8B 112.46(17) . . ?
C8A C8B C2A 105.02(15) . . ?
C8A C8B C5A 116.54(16) . . ?
C2A C8B C5A 101.08(14) . . ?
C8A C8B H8BA 111.2 . . ?
C2A C8B H8BA 111.2 . . ?
C5A C8B H8BA 111.2 . . ?
C11 C10 C2 132.1(4) . . ?
C11 C10 H10A 113.9 . . ?
C2 C10 H10A 113.9 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C13 C12 C8A 126.5(2) . . ?
C13 C12 H12A 116.7 . . ?
C8A C12 H12A 116.7 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
O2 C14 O3 124.4(2) . . ?
O2 C14 C4 122.5(2) . . ?
O3 C14 C4 113.09(18) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 O5 124.6(2) . . ?
O4 C16 C5 122.95(19) . . ?
O5 C16 C5 112.43(17) . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8A O1 C2 C10 152.5(2) . . . . ?
C8A O1 C2 C2A 27.9(2) . . . . ?
O1 C2 C2A C3 -127.93(18) . . . . ?
C10 C2 C2A C3 109.3(2) . . . . ?
O1 C2 C2A C8B -18.3(2) . . . . ?
C10 C2 C2A C8B -141.1(2) . . . . ?
C5A O9 C3 C4 -51.39(16) . . . . ?
C5A O9 C3 C2A 58.71(16) . . . . ?
C2 C2A C3 O9 75.87(19) . . . . ?
C8B C2A C3 O9 -35.92(17) . . . . ?
C2 C2A C3 C4 -177.57(16) . . . . ?
C8B C2A C3 C4 70.65(18) . . . . ?
O9 C3 C4 C5 32.51(19) . . . . ?
C2A C3 C4 C5 -74.1(2) . . . . ?
O9 C3 C4 C14 -154.34(17) . . . . ?
C2A C3 C4 C14 99.1(2) . . . . ?
C14 C4 C5 C16 -1.3(4) . . . . ?
C3 C4 C5 C16 170.71(19) . . . . ?
C14 C4 C5 C5A -171.8(2) . . . . ?
C3 C4 C5 C5A 0.2(2) . . . . ?
C3 O9 C5A C6 174.14(16) . . . . ?
C3 O9 C5A C5 50.52(16) . . . . ?
C3 O9 C5A C8B -57.71(16) . . . . ?
C4 C5 C5A O9 -32.33(19) . . . . ?
C16 C5 C5A O9 156.30(17) . . . . ?
C4 C5 C5A C6 -152.92(17) . . . . ?
C16 C5 C5A C6 35.7(3) . . . . ?
C4 C5 C5A C8B 72.38(18) . . . . ?
C16 C5 C5A C8B -99.0(2) . . . . ?
O9 C5A C6 S7 81.21(19) . . . . ?
C5 C5A C6 S7 -164.69(14) . . . . ?
C8B C5A C6 S7 -36.5(2) . . . . ?
C8 S7 C6 C5A -11.60(19) . . . . ?
C6 S7 C8 C8A 58.78(19) . . . . ?
C2 O1 C8A C12 -144.94(19) . . . . ?
C2 O1 C8A C8 95.2(2) . . . . ?
C2 O1 C8A C8B -25.3(2) . . . . ?
S7 C8 C8A O1 -173.71(14) . . . . ?
S7 C8 C8A C12 68.7(2) . . . . ?
S7 C8 C8A C8B -57.5(2) . . . . ?
O1 C8A C8B C2A 12.23(19) . . . . ?
C12 C8A C8B C2A 129.02(18) . . . . ?
C8 C8A C8B C2A -105.24(19) . . . . ?
O1 C8A C8B C5A 123.12(17) . . . . ?
C12 C8A C8B C5A -120.10(19) . . . . ?
C8 C8A C8B C5A 5.6(2) . . . . ?
C2 C2A C8B C8A 3.43(19) . . . . ?
C3 C2A C8B C8A 122.14(16) . . . . ?
C2 C2A C8B C5A -118.18(16) . . . . ?
C3 C2A C8B C5A 0.54(18) . . . . ?
O9 C5A C8B C8A -78.70(18) . . . . ?
C6 C5A C8B C8A 44.4(2) . . . . ?
C5 C5A C8B C8A 177.32(14) . . . . ?
O9 C5A C8B C2A 34.45(17) . . . . ?
C6 C5A C8B C2A 157.55(17) . . . . ?
C5 C5A C8B C2A -69.54(16) . . . . ?
O1 C2 C10 C11 -8.0(5) . . . . ?
C2A C2 C10 C11 112.5(4) . . . . ?
O1 C8A C12 C13 9.1(3) . . . . ?
C8 C8A C12 C13 126.9(3) . . . . ?
C8B C8A C12 C13 -106.5(3) . . . . ?
C15 O3 C14 O2 6.4(4) . . . . ?
C15 O3 C14 C4 -174.8(2) . . . . ?
C5 C4 C14 O2 -169.4(2) . . . . ?
C3 C4 C14 O2 19.6(3) . . . . ?
C5 C4 C14 O3 11.7(3) . . . . ?
C3 C4 C14 O3 -159.25(18) . . . . ?
C17 O5 C16 O4 6.3(4) . . . . ?
C17 O5 C16 C5 -175.7(2) . . . . ?
C4 C5 C16 O4 -123.6(3) . . . . ?
C5A C5 C16 O4 45.4(3) . . . . ?
C4 C5 C16 O5 58.3(3) . . . . ?
C5A C5 C16 O5 -132.6(2) . . . . ?

_refine_diff_density_max         0.535
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.049



# start Validation Reply Form
_vrf_PLAT910_16b                 
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 12 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_9f
_database_code_depnum_ccdc_archive 'CCDC 2089292'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H21 N O6'
_chemical_formula_sum            'C16 H21 N O6'
_chemical_formula_weight         323.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 '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 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   8.2202(16)
_cell_length_b                   18.800(4)
_cell_length_c                   19.520(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3016.6(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      3.9
_cell_measurement_theta_max      36.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.233
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   'Scala (Evans, 2006)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96990
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29389
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_av_R_equivalents  0.0862
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.957
_diffrn_reflns_theta_max         38.490
_diffrn_reflns_theta_full        35.587
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3142
_reflns_number_gt                2617
_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       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  SHELXTL

_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)+(0.0642P)²+1.5P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0065(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3142
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1262
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.41611(13) 0.61067(5) 0.51531(5) 0.0189(3) Uani 1 1 d . . . . .
O2 O 0.64302(14) 0.52612(5) 0.58078(5) 0.0199(3) Uani 1 1 d . . . . .
O3 O 0.13998(15) 0.66562(6) 0.69659(6) 0.0256(3) Uani 1 1 d . . . . .
O4 O 0.02105(15) 0.74489(6) 0.62578(5) 0.0247(3) Uani 1 1 d . . . . .
O5 O 0.34888(15) 0.79606(6) 0.65871(6) 0.0285(3) Uani 1 1 d . . . . .
O6 O 0.53176(15) 0.82414(6) 0.57708(6) 0.0256(3) Uani 1 1 d . . . . .
C1 C 0.4120(2) 0.46065(8) 0.62854(8) 0.0216(4) Uani 1 1 d . . . . .
H1A H 0.4769 0.4166 0.6231 0.026 Uiso 1 1 calc R U . . .
H1B H 0.3461 0.4555 0.6707 0.026 Uiso 1 1 calc R U . . .
N2 N 0.30156(18) 0.46737(7) 0.56962(6) 0.0212(3) Uani 1 1 d . . . . .
H2 H 0.360(2) 0.4648(9) 0.5293(10) 0.025 Uiso 1 1 d . U . . .
C3 C 0.2113(2) 0.53472(8) 0.57000(8) 0.0207(4) Uani 1 1 d . . . . .
H3A H 0.1332 0.5339 0.6086 0.025 Uiso 1 1 calc R U . . .
H3B H 0.1476 0.5381 0.5271 0.025 Uiso 1 1 calc R U . . .
C3A C 0.3159(2) 0.60085(8) 0.57643(7) 0.0184(3) Uani 1 1 d . . . . .
C4 C 0.2255(2) 0.67341(7) 0.57677(7) 0.0186(3) Uani 1 1 d . . . . .
H4 H 0.1455 0.6719 0.5382 0.022 Uiso 1 1 calc R U . . .
C5 C 0.3659(2) 0.72540(8) 0.55408(7) 0.0194(3) Uani 1 1 d . . . . .
H5 H 0.3334 0.7476 0.5096 0.023 Uiso 1 1 calc R U . . .
C6 C 0.5072(2) 0.67137(7) 0.53926(8) 0.0199(4) Uani 1 1 d . . . . .
H6 H 0.5889 0.6893 0.5054 0.024 Uiso 1 1 calc R U . . .
C6A C 0.5832(2) 0.64562(8) 0.60731(7) 0.0193(3) Uani 1 1 d . . . . .
H6A H 0.6091 0.6856 0.6392 0.023 Uiso 1 1 calc R U . . .
C7 C 0.7237(2) 0.59119(8) 0.60134(8) 0.0209(4) Uani 1 1 d . . . . .
H7 H 0.8125 0.6064 0.5695 0.025 Uiso 1 1 calc R U . . .
C8 C 0.7844(2) 0.57161(8) 0.67400(8) 0.0239(4) Uani 1 1 d . . . . .
H8A H 0.7959 0.6143 0.7032 0.029 Uiso 1 1 calc R U . . .
H8B H 0.8896 0.5460 0.6723 0.029 Uiso 1 1 calc R U . . .
C9 C 0.6445(2) 0.52234(8) 0.69977(7) 0.0234(4) Uani 1 1 d . . . . .
H9A H 0.6846 0.4738 0.7097 0.028 Uiso 1 1 calc R U . . .
H9B H 0.5917 0.5420 0.7413 0.028 Uiso 1 1 calc R U . . .
C9A C 0.5275(2) 0.52289(8) 0.63773(7) 0.0197(4) Uani 1 1 d . . . . .
C9B C 0.4436(2) 0.59662(8) 0.63466(7) 0.0183(3) Uani 1 1 d . . . . .
H9C H 0.3999 0.6124 0.6800 0.022 Uiso 1 1 calc R U . . .
C10 C 0.1305(2) 0.69318(8) 0.64074(7) 0.0199(3) Uani 1 1 d . . . . .
C11 C -0.0634(2) 0.77388(9) 0.68491(9) 0.0288(4) Uani 1 1 d . . . . .
H11A H -0.1410 0.8102 0.6698 0.043 Uiso 1 1 calc R U . . .
H11B H 0.0158 0.7954 0.7162 0.043 Uiso 1 1 calc R U . . .
H11C H -0.1218 0.7357 0.7086 0.043 Uiso 1 1 calc R U . . .
C12 C 0.40985(19) 0.78464(7) 0.60336(7) 0.0193(3) Uani 1 1 d . . . . .
C13 C 0.5765(2) 0.88669(8) 0.61661(9) 0.0271(4) Uani 1 1 d . . . . .
H13A H 0.6709 0.9097 0.5954 0.041 Uiso 1 1 calc R U . . .
H13B H 0.6039 0.8725 0.6635 0.041 Uiso 1 1 calc R U . . .
H13C H 0.4849 0.9200 0.6176 0.041 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.4425(18) . ?
O1 C3A 1.4615(17) . ?
O2 C7 1.4483(18) . ?
O2 C9A 1.4632(18) . ?
O3 C10 1.2095(18) . ?
O4 C10 1.3562(19) . ?
O4 C11 1.4528(19) . ?
O5 C12 1.2101(18) . ?
O6 C12 1.3487(19) . ?
O6 C13 1.4538(18) . ?
C1 N2 1.471(2) . ?
C1 C9A 1.517(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C3 1.468(2) . ?
N2 H2 0.922(19) . ?
C3 C3A 1.517(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C9B 1.549(2) . ?
C3A C4 1.553(2) . ?
C4 C10 1.519(2) . ?
C4 C5 1.576(2) . ?
C4 H4 1.0000 . ?
C5 C12 1.515(2) . ?
C5 C6 1.570(2) . ?
C5 H5 1.0000 . ?
C6 C6A 1.546(2) . ?
C6 H6 1.0000 . ?
C6A C7 1.547(2) . ?
C6A C9B 1.565(2) . ?
C6A H6A 1.0000 . ?
C7 C8 1.548(2) . ?
C7 H7 1.0000 . ?
C8 C9 1.560(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C9A 1.546(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9A C9B 1.549(2) . ?
C9B H9C 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C3A 97.34(10) . . ?
C7 O2 C9A 96.99(10) . . ?
C10 O4 C11 114.50(12) . . ?
C12 O6 C13 115.56(12) . . ?
N2 C1 C9A 114.37(12) . . ?
N2 C1 H1A 108.7 . . ?
C9A C1 H1A 108.7 . . ?
N2 C1 H1B 108.7 . . ?
C9A C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C3 N2 C1 112.47(12) . . ?
C3 N2 H2 108.2(11) . . ?
C1 N2 H2 110.0(12) . . ?
N2 C3 C3A 114.91(14) . . ?
N2 C3 H3A 108.5 . . ?
C3A C3 H3A 108.5 . . ?
N2 C3 H3B 108.5 . . ?
C3A C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
O1 C3A C3 110.82(11) . . ?
O1 C3A C9B 102.91(12) . . ?
C3 C3A C9B 113.74(12) . . ?
O1 C3A C4 99.34(10) . . ?
C3 C3A C4 116.68(14) . . ?
C9B C3A C4 111.48(11) . . ?
C10 C4 C3A 117.67(12) . . ?
C10 C4 C5 117.12(12) . . ?
C3A C4 C5 101.12(12) . . ?
C10 C4 H4 106.7 . . ?
C3A C4 H4 106.7 . . ?
C5 C4 H4 106.7 . . ?
C12 C5 C6 114.60(13) . . ?
C12 C5 C4 116.86(12) . . ?
C6 C5 C4 101.09(11) . . ?
C12 C5 H5 107.9 . . ?
C6 C5 H5 107.9 . . ?
C4 C5 H5 107.9 . . ?
O1 C6 C6A 103.92(11) . . ?
O1 C6 C5 100.83(12) . . ?
C6A C6 C5 110.09(12) . . ?
O1 C6 H6 113.6 . . ?
C6A C6 H6 113.6 . . ?
C5 C6 H6 113.6 . . ?
C6 C6A C7 116.38(12) . . ?
C6 C6A C9B 100.41(12) . . ?
C7 C6A C9B 100.58(11) . . ?
C6 C6A H6A 112.7 . . ?
C7 C6A H6A 112.7 . . ?
C9B C6A H6A 112.7 . . ?
O2 C7 C8 101.58(11) . . ?
O2 C7 C6A 103.74(12) . . ?
C8 C7 C6A 109.19(12) . . ?
O2 C7 H7 113.7 . . ?
C8 C7 H7 113.7 . . ?
C6A C7 H7 113.7 . . ?
C7 C8 C9 101.48(13) . . ?
C7 C8 H8A 111.5 . . ?
C9 C8 H8A 111.5 . . ?
C7 C8 H8B 111.5 . . ?
C9 C8 H8B 111.5 . . ?
H8A C8 H8B 109.3 . . ?
C9A C9 C8 101.65(12) . . ?
C9A C9 H9A 111.4 . . ?
C8 C9 H9A 111.4 . . ?
C9A C9 H9B 111.4 . . ?
C8 C9 H9B 111.4 . . ?
H9A C9 H9B 109.3 . . ?
O2 C9A C1 110.37(11) . . ?
O2 C9A C9 101.06(12) . . ?
C1 C9A C9 118.46(12) . . ?
O2 C9A C9B 102.84(11) . . ?
C1 C9A C9B 114.00(13) . . ?
C9 C9A C9B 108.25(12) . . ?
C9A C9B C3A 112.09(12) . . ?
C9A C9B C6A 102.32(12) . . ?
C3A C9B C6A 102.50(11) . . ?
C9A C9B H9C 113.0 . . ?
C3A C9B H9C 113.0 . . ?
C6A C9B H9C 113.0 . . ?
O3 C10 O4 122.95(14) . . ?
O3 C10 C4 127.07(14) . . ?
O4 C10 C4 109.84(12) . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C12 O6 123.34(14) . . ?
O5 C12 C5 126.76(14) . . ?
O6 C12 C5 109.89(12) . . ?
O6 C13 H13A 109.5 . . ?
O6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A C1 N2 C3 -52.94(18) . . . . ?
C1 N2 C3 C3A 52.92(17) . . . . ?
C6 O1 C3A C3 -175.28(12) . . . . ?
C6 O1 C3A C9B -53.34(12) . . . . ?
C6 O1 C3A C4 61.40(13) . . . . ?
N2 C3 C3A O1 67.11(16) . . . . ?
N2 C3 C3A C9B -48.25(17) . . . . ?
N2 C3 C3A C4 179.78(12) . . . . ?
O1 C3A C4 C10 -167.93(12) . . . . ?
C3 C3A C4 C10 73.00(17) . . . . ?
C9B C3A C4 C10 -60.00(18) . . . . ?
O1 C3A C4 C5 -39.05(13) . . . . ?
C3 C3A C4 C5 -158.11(12) . . . . ?
C9B C3A C4 C5 68.89(14) . . . . ?
C10 C4 C5 C12 8.54(19) . . . . ?
C3A C4 C5 C12 -120.70(13) . . . . ?
C10 C4 C5 C6 133.62(13) . . . . ?
C3A C4 C5 C6 4.38(13) . . . . ?
C3A O1 C6 C6A 55.61(13) . . . . ?
C3A O1 C6 C5 -58.45(12) . . . . ?
C12 C5 C6 O1 158.80(11) . . . . ?
C4 C5 C6 O1 32.20(13) . . . . ?
C12 C5 C6 C6A 49.48(16) . . . . ?
C4 C5 C6 C6A -77.12(14) . . . . ?
O1 C6 C6A C7 72.10(16) . . . . ?
C5 C6 C6A C7 179.36(12) . . . . ?
O1 C6 C6A C9B -35.32(14) . . . . ?
C5 C6 C6A C9B 71.94(13) . . . . ?
C9A O2 C7 C8 57.57(13) . . . . ?
C9A O2 C7 C6A -55.73(12) . . . . ?
C6 C6A C7 O2 -72.30(15) . . . . ?
C9B C6A C7 O2 35.02(13) . . . . ?
C6 C6A C7 C8 180.00(13) . . . . ?
C9B C6A C7 C8 -72.67(14) . . . . ?
O2 C7 C8 C9 -34.65(14) . . . . ?
C6A C7 C8 C9 74.51(14) . . . . ?
C7 C8 C9 C9A -0.52(14) . . . . ?
C7 O2 C9A C1 176.04(12) . . . . ?
C7 O2 C9A C9 -57.76(12) . . . . ?
C7 O2 C9A C9B 54.06(13) . . . . ?
N2 C1 C9A O2 -66.48(16) . . . . ?
N2 C1 C9A C9 177.79(13) . . . . ?
N2 C1 C9A C9B 48.65(17) . . . . ?
C8 C9 C9A O2 35.06(13) . . . . ?
C8 C9 C9A C1 155.69(13) . . . . ?
C8 C9 C9A C9B -72.56(14) . . . . ?
O2 C9A C9B C3A 76.99(15) . . . . ?
C1 C9A C9B C3A -42.50(16) . . . . ?
C9 C9A C9B C3A -176.61(12) . . . . ?
O2 C9A C9B C6A -32.14(13) . . . . ?
C1 C9A C9B C6A -151.63(12) . . . . ?
C9 C9A C9B C6A 74.26(14) . . . . ?
O1 C3A C9B C9A -77.84(14) . . . . ?
C3 C3A C9B C9A 42.10(17) . . . . ?
C4 C3A C9B C9A 176.55(12) . . . . ?
O1 C3A C9B C6A 31.18(13) . . . . ?
C3 C3A C9B C6A 151.12(12) . . . . ?
C4 C3A C9B C6A -74.43(14) . . . . ?
C6 C6A C9B C9A 118.26(11) . . . . ?
C7 C6A C9B C9A -1.33(13) . . . . ?
C6 C6A C9B C3A 1.98(13) . . . . ?
C7 C6A C9B C3A -117.61(12) . . . . ?
C11 O4 C10 O3 10.8(2) . . . . ?
C11 O4 C10 C4 -173.06(13) . . . . ?
C3A C4 C10 O3 14.8(2) . . . . ?
C5 C4 C10 O3 -106.09(19) . . . . ?
C3A C4 C10 O4 -161.11(13) . . . . ?
C5 C4 C10 O4 78.00(16) . . . . ?
C13 O6 C12 O5 -5.8(2) . . . . ?
C13 O6 C12 C5 174.90(13) . . . . ?
C6 C5 C12 O5 -117.52(17) . . . . ?
C4 C5 C12 O5 0.4(2) . . . . ?
C6 C5 C12 O6 61.72(16) . . . . ?
C4 C5 C12 O6 179.69(12) . . . . ?

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.068

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_16c
_database_code_depnum_ccdc_archive 'CCDC 2089296'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 O8 S'
_chemical_formula_sum            'C18 H20 O8 S'
_chemical_formula_weight         396.40

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.4286(2)
_cell_length_b                   10.8270(3)
_cell_length_c                   11.7651(3)
_cell_angle_alpha                114.4500(10)
_cell_angle_beta                 90.1320(10)
_cell_angle_gamma                110.6300(10)
_cell_volume                     900.75(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7587
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      32.60

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.225
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16241
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.709
_diffrn_reflns_theta_max         32.661
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             6515
_reflns_number_gt                5554
_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, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'

_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)+(0.0419P)²+0.2636P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6515
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0890
_refine_ls_wR_factor_gt          0.0832
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.34265(12) 0.85353(10) 0.30513(9) 0.01183(16) Uani 1 1 d . . . . .
H1A H 0.3233 0.9270 0.2836 0.014 Uiso 1 1 calc R U . . .
H1B H 0.4584 0.9018 0.3579 0.014 Uiso 1 1 calc R U . . .
S2 S 0.18786(3) 0.80548(3) 0.39746(2) 0.01073(6) Uani 1 1 d . . . . .
O1 O 0.25252(10) 0.91627(8) 0.52699(7) 0.01719(15) Uani 1 1 d . . . . .
O2 O 0.02051(9) 0.77932(9) 0.34021(8) 0.01638(14) Uani 1 1 d . . . . .
C3 C 0.18388(12) 0.63488(11) 0.38631(9) 0.01207(16) Uani 1 1 d . . . . .
H3A H 0.1836 0.6377 0.4715 0.014 Uiso 1 1 calc R U . . .
H3B H 0.0763 0.5542 0.3305 0.014 Uiso 1 1 calc R U . . .
C3A C 0.33618(12) 0.60291(10) 0.33444(9) 0.01012(15) Uani 1 1 d . . . . .
C4 C 0.35265(12) 0.46472(10) 0.33068(9) 0.01114(16) Uani 1 1 d . . . . .
C5 C 0.52049(12) 0.49040(11) 0.33295(9) 0.01181(16) Uani 1 1 d . . . . .
C6 C 0.60523(12) 0.64324(10) 0.34002(9) 0.01147(16) Uani 1 1 d . . . . .
H6 H 0.7311 0.6947 0.3758 0.014 Uiso 1 1 calc R U . . .
C6A C 0.55525(12) 0.62707(10) 0.20603(9) 0.01084(16) Uani 1 1 d . . . . .
H6A H 0.5763 0.5443 0.1374 0.013 Uiso 1 1 calc R U . . .
C7 C 0.63353(12) 0.77133(10) 0.19334(9) 0.01117(16) Uani 1 1 d . . . . .
H7 H 0.6773 0.8556 0.2801 0.013 Uiso 1 1 calc R U . . .
O8 O 0.49335(9) 0.78183(8) 0.13388(7) 0.01223(13) Uani 1 1 d . . . . .
C8A C 0.34245(12) 0.72496(10) 0.18079(9) 0.01089(16) Uani 1 1 d . . . . .
C8B C 0.36109(12) 0.59762(10) 0.20167(9) 0.01019(16) Uani 1 1 d . . . . .
H8B H 0.2882 0.4992 0.1318 0.012 Uiso 1 1 calc R U . . .
O7 O 0.49803(9) 0.71487(8) 0.41153(7) 0.01129(13) Uani 1 1 d . . . . .
C9 C 0.20404(12) 0.33143(10) 0.31232(9) 0.01179(16) Uani 1 1 d . . . . .
O3 O 0.06406(10) 0.29782(9) 0.25531(8) 0.01754(15) Uani 1 1 d . . . . .
O4 O 0.24247(10) 0.25611(8) 0.36515(7) 0.01476(14) Uani 1 1 d . . . . .
C10 C 0.10731(15) 0.11781(12) 0.34217(12) 0.0212(2) Uani 1 1 d . . . . .
H10A H 0.1390 0.0798 0.3973 0.032 Uiso 1 1 calc R U . . .
H10B H 0.0908 0.0471 0.2533 0.032 Uiso 1 1 calc R U . . .
H10C H 0.0001 0.1325 0.3602 0.032 Uiso 1 1 calc R U . . .
C11 C 0.61755(12) 0.39744(11) 0.32462(9) 0.01238(17) Uani 1 1 d . . . . .
O5 O 0.75832(10) 0.44730(9) 0.38793(8) 0.01783(15) Uani 1 1 d . . . . .
O6 O 0.53542(10) 0.25776(8) 0.24020(7) 0.01510(14) Uani 1 1 d . . . . .
C12 C 0.61887(15) 0.15904(12) 0.23453(11) 0.0190(2) Uani 1 1 d . . . . .
H12A H 0.5556 0.0616 0.1642 0.029 Uiso 1 1 calc R U . . .
H12B H 0.6198 0.1508 0.3144 0.029 Uiso 1 1 calc R U . . .
H12C H 0.7374 0.1981 0.2211 0.029 Uiso 1 1 calc R U . . .
C13 C 0.77574(13) 0.78026(11) 0.11786(10) 0.01382(17) Uani 1 1 d . . . . .
H13 H 0.8717 0.7658 0.1441 0.017 Uiso 1 1 calc R U . . .
C14 C 0.77937(15) 0.80660(13) 0.01750(11) 0.0201(2) Uani 1 1 d . . . . .
H14A H 0.6860 0.8217 -0.0120 0.024 Uiso 1 1 calc R U . . .
H14B H 0.8753 0.8104 -0.0251 0.024 Uiso 1 1 calc R U . . .
C15 C 0.18686(13) 0.67182(11) 0.08399(10) 0.01414(17) Uani 1 1 d . . . . .
H15 H 0.0767 0.6304 0.1028 0.017 Uiso 1 1 calc R U . . .
C16 C 0.19350(15) 0.67901(14) -0.02565(11) 0.0229(2) Uani 1 1 d . . . . .
H16A H 0.3016 0.7198 -0.0474 0.028 Uiso 1 1 calc R U . . .
H16B H 0.0901 0.6434 -0.0825 0.028 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C8A 1.5460(14) . ?
C1 S2 1.7745(10) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
S2 O2 1.4421(8) . ?
S2 O1 1.4425(8) . ?
S2 C3 1.7849(10) . ?
C3 C3A 1.5106(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A O7 1.4394(11) . ?
C3A C4 1.5334(13) . ?
C3A C8B 1.5568(13) . ?
C4 C5 1.3400(13) . ?
C4 C9 1.4714(13) . ?
C5 C11 1.4802(13) . ?
C5 C6 1.5193(13) . ?
C6 O7 1.4431(12) . ?
C6 C6A 1.5523(13) . ?
C6 H6 1.0000 . ?
C6A C7 1.5376(13) . ?
C6A C8B 1.5494(13) . ?
C6A H6A 1.0000 . ?
C7 O8 1.4335(11) . ?
C7 C13 1.4930(13) . ?
C7 H7 1.0000 . ?
O8 C8A 1.4263(11) . ?
C8A C15 1.5056(13) . ?
C8A C8B 1.5552(13) . ?
C8B H8B 1.0000 . ?
C9 O3 1.2109(12) . ?
C9 O4 1.3270(12) . ?
O4 C10 1.4403(13) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O5 1.2106(12) . ?
C11 O6 1.3298(12) . ?
O6 C12 1.4535(12) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.3226(15) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9500 . ?
C14 H14B 0.9500 . ?
C15 C16 1.3241(15) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9500 . ?
C16 H16B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8A C1 S2 115.85(7) . . ?
C8A C1 H1A 108.3 . . ?
S2 C1 H1A 108.3 . . ?
C8A C1 H1B 108.3 . . ?
S2 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
O2 S2 O1 117.65(5) . . ?
O2 S2 C1 109.42(5) . . ?
O1 S2 C1 107.36(5) . . ?
O2 S2 C3 107.95(5) . . ?
O1 S2 C3 108.91(5) . . ?
C1 S2 C3 104.80(4) . . ?
C3A C3 S2 112.29(7) . . ?
C3A C3 H3A 109.1 . . ?
S2 C3 H3A 109.1 . . ?
C3A C3 H3B 109.1 . . ?
S2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
O7 C3A C3 112.49(8) . . ?
O7 C3A C4 100.99(7) . . ?
C3 C3A C4 116.48(8) . . ?
O7 C3A C8B 101.64(7) . . ?
C3 C3A C8B 116.81(8) . . ?
C4 C3A C8B 106.31(7) . . ?
C5 C4 C9 131.07(9) . . ?
C5 C4 C3A 105.03(8) . . ?
C9 C4 C3A 123.49(8) . . ?
C4 C5 C11 131.68(9) . . ?
C4 C5 C6 105.67(8) . . ?
C11 C5 C6 122.59(8) . . ?
O7 C6 C5 101.45(7) . . ?
O7 C6 C6A 101.79(7) . . ?
C5 C6 C6A 106.16(8) . . ?
O7 C6 H6 115.2 . . ?
C5 C6 H6 115.2 . . ?
C6A C6 H6 115.2 . . ?
C7 C6A C8B 104.15(7) . . ?
C7 C6A C6 113.90(8) . . ?
C8B C6A C6 101.03(7) . . ?
C7 C6A H6A 112.3 . . ?
C8B C6A H6A 112.3 . . ?
C6 C6A H6A 112.3 . . ?
O8 C7 C13 109.73(8) . . ?
O8 C7 C6A 105.42(7) . . ?
C13 C7 C6A 115.11(8) . . ?
O8 C7 H7 108.8 . . ?
C13 C7 H7 108.8 . . ?
C6A C7 H7 108.8 . . ?
C8A O8 C7 108.14(7) . . ?
O8 C8A C15 108.76(8) . . ?
O8 C8A C1 106.64(7) . . ?
C15 C8A C1 110.54(8) . . ?
O8 C8A C8B 105.13(7) . . ?
C15 C8A C8B 112.29(8) . . ?
C1 C8A C8B 113.10(7) . . ?
C6A C8B C8A 104.50(7) . . ?
C6A C8B C3A 101.18(7) . . ?
C8A C8B C3A 115.75(8) . . ?
C6A C8B H8B 111.6 . . ?
C8A C8B H8B 111.6 . . ?
C3A C8B H8B 111.6 . . ?
C3A O7 C6 96.37(7) . . ?
O3 C9 O4 125.38(9) . . ?
O3 C9 C4 122.28(9) . . ?
O4 C9 C4 112.34(8) . . ?
C9 O4 C10 115.52(8) . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O5 C11 O6 124.92(9) . . ?
O5 C11 C5 122.03(9) . . ?
O6 C11 C5 113.04(8) . . ?
C11 O6 C12 115.44(8) . . ?
O6 C12 H12A 109.5 . . ?
O6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C7 125.50(10) . . ?
C14 C13 H13 117.2 . . ?
C7 C13 H13 117.2 . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
C16 C15 C8A 124.32(10) . . ?
C16 C15 H15 117.8 . . ?
C8A C15 H15 117.8 . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?

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
C8A C1 S2 O2 -76.28(8) . . . . ?
C8A C1 S2 O1 154.98(7) . . . . ?
C8A C1 S2 C3 39.26(8) . . . . ?
O2 S2 C3 C3A 131.04(7) . . . . ?
O1 S2 C3 C3A -100.16(7) . . . . ?
C1 S2 C3 C3A 14.48(8) . . . . ?
S2 C3 C3A O7 59.50(9) . . . . ?
S2 C3 C3A C4 175.40(7) . . . . ?
S2 C3 C3A C8B -57.49(10) . . . . ?
O7 C3A C4 C5 -33.33(9) . . . . ?
C3 C3A C4 C5 -155.47(8) . . . . ?
C8B C3A C4 C5 72.40(9) . . . . ?
O7 C3A C4 C9 153.30(9) . . . . ?
C3 C3A C4 C9 31.15(13) . . . . ?
C8B C3A C4 C9 -100.98(10) . . . . ?
C9 C4 C5 C11 -3.67(19) . . . . ?
C3A C4 C5 C11 -176.33(10) . . . . ?
C9 C4 C5 C6 173.49(10) . . . . ?
C3A C4 C5 C6 0.82(10) . . . . ?
C4 C5 C6 O7 31.87(9) . . . . ?
C11 C5 C6 O7 -150.65(9) . . . . ?
C4 C5 C6 C6A -74.13(9) . . . . ?
C11 C5 C6 C6A 103.35(10) . . . . ?
O7 C6 C6A C7 75.64(9) . . . . ?
C5 C6 C6A C7 -178.59(8) . . . . ?
O7 C6 C6A C8B -35.38(8) . . . . ?
C5 C6 C6A C8B 70.38(8) . . . . ?
C8B C6A C7 O8 -22.54(9) . . . . ?
C6 C6A C7 O8 -131.65(8) . . . . ?
C8B C6A C7 C13 -143.60(8) . . . . ?
C6 C6A C7 C13 107.29(9) . . . . ?
C13 C7 O8 C8A 160.87(8) . . . . ?
C6A C7 O8 C8A 36.36(9) . . . . ?
C7 O8 C8A C15 -154.95(8) . . . . ?
C7 O8 C8A C1 85.82(8) . . . . ?
C7 O8 C8A C8B -34.51(9) . . . . ?
S2 C1 C8A O8 -169.78(6) . . . . ?
S2 C1 C8A C15 72.15(9) . . . . ?
S2 C1 C8A C8B -54.72(10) . . . . ?
C7 C6A C8B C8A 2.39(9) . . . . ?
C6 C6A C8B C8A 120.73(7) . . . . ?
C7 C6A C8B C3A -118.18(8) . . . . ?
C6 C6A C8B C3A 0.16(8) . . . . ?
O8 C8A C8B C6A 18.58(9) . . . . ?
C15 C8A C8B C6A 136.68(8) . . . . ?
C1 C8A C8B C6A -97.38(9) . . . . ?
O8 C8A C8B C3A 128.90(8) . . . . ?
C15 C8A C8B C3A -113.01(9) . . . . ?
C1 C8A C8B C3A 12.94(11) . . . . ?
O7 C3A C8B C6A 35.18(8) . . . . ?
C3 C3A C8B C6A 157.97(8) . . . . ?
C4 C3A C8B C6A -70.08(8) . . . . ?
O7 C3A C8B C8A -77.08(9) . . . . ?
C3 C3A C8B C8A 45.72(11) . . . . ?
C4 C3A C8B C8A 177.66(7) . . . . ?
C3 C3A O7 C6 176.22(7) . . . . ?
C4 C3A O7 C6 51.32(8) . . . . ?
C8B C3A O7 C6 -58.07(8) . . . . ?
C5 C6 O7 C3A -51.06(8) . . . . ?
C6A C6 O7 C3A 58.35(8) . . . . ?
C5 C4 C9 O3 -144.16(11) . . . . ?
C3A C4 C9 O3 27.34(15) . . . . ?
C5 C4 C9 O4 36.09(15) . . . . ?
C3A C4 C9 O4 -152.41(9) . . . . ?
O3 C9 O4 C10 5.20(14) . . . . ?
C4 C9 O4 C10 -175.06(8) . . . . ?
C4 C5 C11 O5 -140.87(12) . . . . ?
C6 C5 C11 O5 42.39(14) . . . . ?
C4 C5 C11 O6 40.30(15) . . . . ?
C6 C5 C11 O6 -136.45(9) . . . . ?
O5 C11 O6 C12 5.52(14) . . . . ?
C5 C11 O6 C12 -175.68(8) . . . . ?
O8 C7 C13 C14 5.41(14) . . . . ?
C6A C7 C13 C14 124.09(11) . . . . ?
O8 C8A C15 C16 -0.31(14) . . . . ?
C1 C8A C15 C16 116.44(12) . . . . ?
C8B C8A C15 C16 -116.23(12) . . . . ?

_refine_diff_density_max         0.424
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_XB2
_database_code_depnum_ccdc_archive 'CCDC 2095411'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2021-07-09 deposited with the CCDC.	2021-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H25 N O10'
_chemical_formula_sum            'C21 H25 N O10'
_chemical_formula_weight         451.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 '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 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   24.280(5)
_cell_length_b                   9.4800(19)
_cell_length_c                   17.870(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.83(3)
_cell_angle_gamma                90
_cell_volume                     4064.5(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1000
_cell_measurement_theta_min      3.5
_cell_measurement_theta_max      35.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             1904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.255
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   'Scala (Evans, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96990
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17781
_diffrn_reflns_av_unetI/netI     0.1020
_diffrn_reflns_av_R_equivalents  0.0791
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.444
_diffrn_reflns_theta_max         38.450
_diffrn_reflns_theta_full        35.587
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             4107
_reflns_number_gt                3383
_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       Automar
_computing_cell_refinement       iMosflm
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0477P)²+2.77P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4107
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1419
_refine_ls_wR_factor_gt          0.1314
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
O1 O 0.42614(6) 0.33047(12) 0.23778(6) 0.0274(3) Uani 1 1 d . . . . .
O2 O 0.35567(5) 0.52055(12) 0.23313(5) 0.0181(3) Uani 1 1 d . . . . .
O3 O 0.28814(5) 0.68631(11) 0.29386(6) 0.0175(3) Uani 1 1 d . . . . .
O4 O 0.24273(5) 0.76932(13) 0.40116(6) 0.0234(3) Uani 1 1 d . . . . .
O5 O 0.36781(5) 1.01491(11) 0.21852(6) 0.0196(3) Uani 1 1 d . . . . .
O6 O 0.41707(5) 0.85508(11) 0.15947(6) 0.0192(3) Uani 1 1 d . . . . .
O7 O 0.33799(5) 0.25556(13) 0.42105(6) 0.0270(3) Uani 1 1 d . . . . .
O8 O 0.24793(5) 0.31018(13) 0.38028(6) 0.0259(3) Uani 1 1 d . . . . .
O9 O 0.44923(5) 0.59258(14) 0.44824(6) 0.0250(3) Uani 1 1 d . . . . .
O10 O 0.37469(5) 0.51498(12) 0.49618(5) 0.0199(3) Uani 1 1 d . . . . .
C1 C 0.36805(7) 0.83473(16) 0.33992(8) 0.0167(4) Uani 1 1 d . . . . .
H1A H 0.3446 0.9202 0.3299 0.020 Uiso 1 1 calc R U . . .
H1B H 0.3963 0.8531 0.3850 0.020 Uiso 1 1 calc R U . . .
N2 N 0.39616(6) 0.80605(13) 0.27464(7) 0.0166(3) Uani 1 1 d . . . . .
C3 C 0.43081(7) 0.67903(16) 0.27893(8) 0.0167(4) Uani 1 1 d . . . . .
H3A H 0.4635 0.6911 0.3190 0.020 Uiso 1 1 calc R U . . .
H3B H 0.4447 0.6654 0.2302 0.020 Uiso 1 1 calc R U . . .
C3A C 0.39833(7) 0.55048(16) 0.29607(8) 0.0154(4) Uani 1 1 d . . . . .
C4 C 0.42892(8) 0.40838(17) 0.30760(8) 0.0204(4) Uani 1 1 d . . . . .
H4 H 0.4590 0.3913 0.3515 0.024 Uiso 1 1 calc R U . . .
C5 C 0.38406(8) 0.30597(18) 0.28554(9) 0.0227(4) Uani 1 1 d . . . . .
H5 H 0.3822 0.2152 0.3135 0.027 Uiso 1 1 calc R U . . .
C6 C 0.33223(8) 0.39880(17) 0.26306(8) 0.0202(4) Uani 1 1 d . . . . .
H6 H 0.3016 0.3529 0.2276 0.024 Uiso 1 1 calc R U . . .
C6A C 0.31406(7) 0.45875(17) 0.33826(8) 0.0172(4) Uani 1 1 d . . . . .
C7 C 0.26402(7) 0.56414(17) 0.32365(8) 0.0192(4) Uani 1 1 d . . . . .
H7 H 0.2301 0.5264 0.2910 0.023 Uiso 1 1 calc R U . . .
C8 C 0.25401(7) 0.61907(18) 0.40161(8) 0.0199(4) Uani 1 1 d . . . . .
H8 H 0.2410 0.5550 0.4398 0.024 Uiso 1 1 calc R U . . .
C9 C 0.29907(7) 0.72014(17) 0.42304(8) 0.0174(4) Uani 1 1 d . . . . .
H9 H 0.3185 0.7280 0.4764 0.021 Uiso 1 1 calc R U . . .
C9A C 0.33186(7) 0.71121(16) 0.35570(8) 0.0152(4) Uani 1 1 d . . . . .
C9B C 0.36362(7) 0.56493(16) 0.36310(8) 0.0141(4) Uani 1 1 d . . . . .
C10 C 0.39178(7) 0.90224(16) 0.21718(8) 0.0162(4) Uani 1 1 d . . . . .
C11 C 0.43234(7) 0.95528(16) 0.10227(8) 0.0169(4) Uani 1 1 d . . . . .
C12 C 0.47661(8) 1.05523(19) 0.14181(9) 0.0244(4) Uani 1 1 d . . . . .
H12A H 0.4608 1.1114 0.1794 0.037 Uiso 1 1 calc R U . . .
H12B H 0.4892 1.1181 0.1043 0.037 Uiso 1 1 calc R U . . .
H12C H 0.5083 1.0005 0.1672 0.037 Uiso 1 1 calc R U . . .
C13 C 0.45539(8) 0.85707(18) 0.04710(8) 0.0208(4) Uani 1 1 d . . . . .
H13A H 0.4875 0.8055 0.0738 0.031 Uiso 1 1 calc R U . . .
H13B H 0.4670 0.9126 0.0060 0.031 Uiso 1 1 calc R U . . .
H13C H 0.4264 0.7899 0.0260 0.031 Uiso 1 1 calc R U . . .
C14 C 0.38200(8) 1.0341(2) 0.06128(9) 0.0267(4) Uani 1 1 d . . . . .
H14A H 0.3519 0.9669 0.0447 0.040 Uiso 1 1 calc R U . . .
H14B H 0.3923 1.0827 0.0171 0.040 Uiso 1 1 calc R U . . .
H14C H 0.3694 1.1033 0.0956 0.040 Uiso 1 1 calc R U . . .
C15 C 0.30335(8) 0.33224(17) 0.38696(8) 0.0191(4) Uani 1 1 d . . . . .
C16 C 0.23004(10) 0.1755(2) 0.40713(11) 0.0357(5) Uani 1 1 d . . . . .
H16A H 0.2278 0.1057 0.3663 0.053 Uiso 1 1 calc R U . . .
H16B H 0.1933 0.1864 0.4228 0.053 Uiso 1 1 calc R U . . .
H16C H 0.2570 0.1437 0.4504 0.053 Uiso 1 1 calc R U . . .
C17 C 0.40099(7) 0.55567(16) 0.43951(8) 0.0149(4) Uani 1 1 d . . . . .
C18 C 0.40768(8) 0.5245(2) 0.57165(8) 0.0253(4) Uani 1 1 d . . . . .
H18A H 0.4420 0.4696 0.5730 0.038 Uiso 1 1 calc R U . . .
H18B H 0.3860 0.4870 0.6092 0.038 Uiso 1 1 calc R U . . .
H18C H 0.4171 0.6234 0.5834 0.038 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.4425(18) . ?
O1 C5 1.447(2) . ?
O2 C6 1.4267(19) . ?
O2 C3A 1.436(2) . ?
O3 C9A 1.4295(19) . ?
O3 C7 1.4365(19) . ?
O4 C9 1.441(2) . ?
O4 C8 1.450(2) . ?
O5 C10 1.2185(19) . ?
O6 C10 1.3546(18) . ?
O6 C11 1.4836(17) . ?
O7 C15 1.204(2) . ?
O8 C15 1.349(2) . ?
O8 C16 1.453(2) . ?
O9 C17 1.209(2) . ?
O10 C17 1.3345(18) . ?
O10 C18 1.4618(19) . ?
C1 N2 1.4646(19) . ?
C1 C9A 1.516(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C10 1.3652(19) . ?
N2 C3 1.464(2) . ?
C3 C3A 1.508(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4 1.537(2) . ?
C3A C9B 1.573(2) . ?
C4 C5 1.467(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.538(3) . ?
C5 H5 1.0000 . ?
C6 C6A 1.583(2) . ?
C6 H6 1.0000 . ?
C6A C15 1.527(2) . ?
C6A C7 1.564(2) . ?
C6A C9B 1.579(2) . ?
C7 C8 1.541(2) . ?
C7 H7 1.0000 . ?
C8 C9 1.461(2) . ?
C8 H8 1.0000 . ?
C9 C9A 1.544(2) . ?
C9 H9 1.0000 . ?
C9A C9B 1.582(2) . ?
C9B C17 1.521(2) . ?
C11 C14 1.521(2) . ?
C11 C12 1.523(2) . ?
C11 C13 1.524(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C5 61.03(11) . . ?
C6 O2 C3A 98.48(11) . . ?
C9A O3 C7 98.24(11) . . ?
C9 O4 C8 60.68(11) . . ?
C10 O6 C11 120.24(12) . . ?
C15 O8 C16 116.85(15) . . ?
C17 O10 C18 115.09(13) . . ?
N2 C1 C9A 111.04(12) . . ?
N2 C1 H1A 109.4 . . ?
C9A C1 H1A 109.4 . . ?
N2 C1 H1B 109.4 . . ?
C9A C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C10 N2 C3 124.50(12) . . ?
C10 N2 C1 118.89(13) . . ?
C3 N2 C1 116.44(12) . . ?
N2 C3 C3A 111.15(13) . . ?
N2 C3 H3A 109.4 . . ?
C3A C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
C3A C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
O2 C3A C3 109.72(12) . . ?
O2 C3A C4 101.98(12) . . ?
C3 C3A C4 118.58(14) . . ?
O2 C3A C9B 101.98(13) . . ?
C3 C3A C9B 116.25(12) . . ?
C4 C3A C9B 106.18(11) . . ?
O1 C4 C5 59.64(10) . . ?
O1 C4 C3A 112.04(13) . . ?
C5 C4 C3A 102.73(15) . . ?
O1 C4 H4 121.8 . . ?
C5 C4 H4 121.8 . . ?
C3A C4 H4 121.8 . . ?
O1 C5 C4 59.33(10) . . ?
O1 C5 C6 112.19(13) . . ?
C4 C5 C6 103.62(14) . . ?
O1 C5 H5 121.6 . . ?
C4 C5 H5 121.6 . . ?
C6 C5 H5 121.6 . . ?
O2 C6 C5 101.74(13) . . ?
O2 C6 C6A 101.95(12) . . ?
C5 C6 C6A 107.90(13) . . ?
O2 C6 H6 114.6 . . ?
C5 C6 H6 114.6 . . ?
C6A C6 H6 114.6 . . ?
C15 C6A C7 113.65(13) . . ?
C15 C6A C9B 121.96(13) . . ?
C7 C6A C9B 100.29(13) . . ?
C15 C6A C6 107.21(13) . . ?
C7 C6A C6 113.47(12) . . ?
C9B C6A C6 99.65(12) . . ?
O3 C7 C8 101.10(12) . . ?
O3 C7 C6A 103.09(13) . . ?
C8 C7 C6A 106.93(13) . . ?
O3 C7 H7 114.7 . . ?
C8 C7 H7 114.7 . . ?
C6A C7 H7 114.7 . . ?
O4 C8 C9 59.36(11) . . ?
O4 C8 C7 112.50(12) . . ?
C9 C8 C7 104.06(13) . . ?
O4 C8 H8 121.4 . . ?
C9 C8 H8 121.4 . . ?
C7 C8 H8 121.4 . . ?
O4 C9 C8 59.97(11) . . ?
O4 C9 C9A 112.82(12) . . ?
C8 C9 C9A 102.41(12) . . ?
O4 C9 H9 121.6 . . ?
C8 C9 H9 121.6 . . ?
C9A C9 H9 121.6 . . ?
O3 C9A C1 111.50(12) . . ?
O3 C9A C9 101.60(13) . . ?
C1 C9A C9 119.05(13) . . ?
O3 C9A C9B 102.38(11) . . ?
C1 C9A C9B 113.79(13) . . ?
C9 C9A C9B 106.62(11) . . ?
C17 C9B C3A 111.29(13) . . ?
C17 C9B C6A 122.62(12) . . ?
C3A C9B C6A 101.81(11) . . ?
C17 C9B C9A 109.96(12) . . ?
C3A C9B C9A 108.90(11) . . ?
C6A C9B C9A 101.21(13) . . ?
O5 C10 O6 125.32(13) . . ?
O5 C10 N2 123.57(13) . . ?
O6 C10 N2 111.11(13) . . ?
O6 C11 C14 112.27(14) . . ?
O6 C11 C12 108.18(12) . . ?
C14 C11 C12 112.06(15) . . ?
O6 C11 C13 102.12(12) . . ?
C14 C11 C13 109.65(13) . . ?
C12 C11 C13 112.17(14) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O7 C15 O8 124.13(15) . . ?
O7 C15 C6A 126.56(16) . . ?
O8 C15 C6A 109.03(14) . . ?
O8 C16 H16A 109.5 . . ?
O8 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O8 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O9 C17 O10 123.54(14) . . ?
O9 C17 C9B 122.10(13) . . ?
O10 C17 C9B 114.13(14) . . ?
O10 C18 H18A 109.5 . . ?
O10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A C1 N2 C10 127.89(15) . . . . ?
C9A C1 N2 C3 -56.61(19) . . . . ?
C10 N2 C3 C3A -131.10(15) . . . . ?
C1 N2 C3 C3A 53.68(18) . . . . ?
C6 O2 C3A C3 179.90(12) . . . . ?
C6 O2 C3A C4 53.35(13) . . . . ?
C6 O2 C3A C9B -56.30(13) . . . . ?
N2 C3 C3A O2 67.22(15) . . . . ?
N2 C3 C3A C4 -176.27(12) . . . . ?
N2 C3 C3A C9B -47.77(18) . . . . ?
C5 O1 C4 C3A -92.20(16) . . . . ?
O2 C3A C4 O1 29.50(16) . . . . ?
C3 C3A C4 O1 -91.06(17) . . . . ?
C9B C3A C4 O1 135.90(14) . . . . ?
O2 C3A C4 C5 -32.62(13) . . . . ?
C3 C3A C4 C5 -153.17(13) . . . . ?
C9B C3A C4 C5 73.78(14) . . . . ?
C4 O1 C5 C6 93.09(15) . . . . ?
C3A C4 C5 O1 108.28(12) . . . . ?
O1 C4 C5 C6 -107.94(13) . . . . ?
C3A C4 C5 C6 0.33(14) . . . . ?
C3A O2 C6 C5 -52.86(13) . . . . ?
C3A O2 C6 C6A 58.54(14) . . . . ?
O1 C5 C6 O2 -29.87(16) . . . . ?
C4 C5 C6 O2 32.24(14) . . . . ?
O1 C5 C6 C6A -136.69(13) . . . . ?
C4 C5 C6 C6A -74.58(15) . . . . ?
O2 C6 C6A C15 -164.41(13) . . . . ?
C5 C6 C6A C15 -57.74(17) . . . . ?
O2 C6 C6A C7 69.27(16) . . . . ?
C5 C6 C6A C7 175.94(13) . . . . ?
O2 C6 C6A C9B -36.48(15) . . . . ?
C5 C6 C6A C9B 70.19(15) . . . . ?
C9A O3 C7 C8 53.27(14) . . . . ?
C9A O3 C7 C6A -57.23(13) . . . . ?
C15 C6A C7 O3 166.65(12) . . . . ?
C9B C6A C7 O3 34.83(13) . . . . ?
C6 C6A C7 O3 -70.51(16) . . . . ?
C15 C6A C7 C8 60.55(17) . . . . ?
C9B C6A C7 C8 -71.27(14) . . . . ?
C6 C6A C7 C8 -176.61(13) . . . . ?
C9 O4 C8 C7 -93.45(15) . . . . ?
O3 C7 C8 O4 30.62(17) . . . . ?
C6A C7 C8 O4 138.14(14) . . . . ?
O3 C7 C8 C9 -31.67(16) . . . . ?
C6A C7 C8 C9 75.85(15) . . . . ?
C8 O4 C9 C9A 91.49(14) . . . . ?
C7 C8 C9 O4 108.07(13) . . . . ?
O4 C8 C9 C9A -109.36(12) . . . . ?
C7 C8 C9 C9A -1.29(16) . . . . ?
C7 O3 C9A C1 177.57(12) . . . . ?
C7 O3 C9A C9 -54.58(13) . . . . ?
C7 O3 C9A C9B 55.54(13) . . . . ?
N2 C1 C9A O3 -62.83(17) . . . . ?
N2 C1 C9A C9 179.39(13) . . . . ?
N2 C1 C9A C9B 52.35(17) . . . . ?
O4 C9 C9A O3 -28.24(16) . . . . ?
C8 C9 C9A O3 34.16(15) . . . . ?
O4 C9 C9A C1 94.58(17) . . . . ?
C8 C9 C9A C1 156.98(14) . . . . ?
O4 C9 C9A C9B -135.07(13) . . . . ?
C8 C9 C9A C9B -72.68(15) . . . . ?
O2 C3A C9B C17 163.86(11) . . . . ?
C3 C3A C9B C17 -76.85(17) . . . . ?
C4 C3A C9B C17 57.45(16) . . . . ?
O2 C3A C9B C6A 31.59(14) . . . . ?
C3 C3A C9B C6A 150.88(14) . . . . ?
C4 C3A C9B C6A -74.81(15) . . . . ?
O2 C3A C9B C9A -74.76(14) . . . . ?
C3 C3A C9B C9A 44.52(18) . . . . ?
C4 C3A C9B C9A 178.83(12) . . . . ?
C15 C6A C9B C17 -5.1(2) . . . . ?
C7 C6A C9B C17 121.37(14) . . . . ?
C6 C6A C9B C17 -122.43(14) . . . . ?
C15 C6A C9B C3A 119.99(15) . . . . ?
C7 C6A C9B C3A -113.58(12) . . . . ?
C6 C6A C9B C3A 2.62(14) . . . . ?
C15 C6A C9B C9A -127.74(15) . . . . ?
C7 C6A C9B C9A -1.31(12) . . . . ?
C6 C6A C9B C9A 114.89(12) . . . . ?
O3 C9A C9B C17 -163.61(12) . . . . ?
C1 C9A C9B C17 75.93(15) . . . . ?
C9 C9A C9B C17 -57.33(16) . . . . ?
O3 C9A C9B C3A 74.20(14) . . . . ?
C1 C9A C9B C3A -46.25(16) . . . . ?
C9 C9A C9B C3A -179.52(12) . . . . ?
O3 C9A C9B C6A -32.57(12) . . . . ?
C1 C9A C9B C6A -153.02(12) . . . . ?
C9 C9A C9B C6A 73.72(13) . . . . ?
C11 O6 C10 O5 18.6(2) . . . . ?
C11 O6 C10 N2 -161.82(13) . . . . ?
C3 N2 C10 O5 -171.49(15) . . . . ?
C1 N2 C10 O5 3.6(2) . . . . ?
C3 N2 C10 O6 8.9(2) . . . . ?
C1 N2 C10 O6 -176.00(13) . . . . ?
C10 O6 C11 C14 -59.07(19) . . . . ?
C10 O6 C11 C12 65.10(18) . . . . ?
C10 O6 C11 C13 -176.43(14) . . . . ?
C16 O8 C15 O7 -8.9(2) . . . . ?
C16 O8 C15 C6A 165.38(13) . . . . ?
C7 C6A C15 O7 -161.04(15) . . . . ?
C9B C6A C15 O7 -40.8(2) . . . . ?
C6 C6A C15 O7 72.7(2) . . . . ?
C7 C6A C15 O8 24.90(17) . . . . ?
C9B C6A C15 O8 145.11(14) . . . . ?
C6 C6A C15 O8 -101.31(15) . . . . ?
C18 O10 C17 O9 2.9(2) . . . . ?
C18 O10 C17 C9B -171.69(13) . . . . ?
C3A C9B C17 O9 28.9(2) . . . . ?
C6A C9B C17 O9 149.59(16) . . . . ?
C9A C9B C17 O9 -91.85(18) . . . . ?
C3A C9B C17 O10 -156.39(13) . . . . ?
C6A C9B C17 O10 -35.7(2) . . . . ?
C9A C9B C17 O10 82.85(15) . . . . ?

_refine_diff_density_max         0.426
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.069

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_9a
_database_code_depnum_ccdc_archive 'CCDC 2089291'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 O7'
_chemical_formula_sum            'C16 H20 O7'
_chemical_formula_weight         324.32

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'
O O 0.0106 0.0060 '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                   9.8479(4)
_cell_length_b                   11.0756(5)
_cell_length_c                   13.8648(6)
_cell_angle_alpha                92.988(2)
_cell_angle_beta                 98.882(2)
_cell_angle_gamma                90.550(2)
_cell_volume                     1491.85(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4568
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      26.07

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       '/f and /w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22457
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.207
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             6758
_reflns_number_gt                4428
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0519P)²+0.2103P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6758
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
O2 O 0.18273(13) -0.23927(11) 0.21797(9) 0.0481(3) Uani 1 1 d . . . . .
O3 O 0.53964(14) 0.01222(13) 0.32835(10) 0.0588(4) Uani 1 1 d . . . . .
O4 O 0.48658(14) 0.18995(14) 0.39507(10) 0.0616(4) Uani 1 1 d . . . . .
O5 O 0.48571(13) 0.23974(12) 0.19486(11) 0.0530(4) Uani 1 1 d . . . . .
O6 O 0.31198(13) 0.36033(11) 0.14341(10) 0.0473(3) Uani 1 1 d . . . . .
O10 O 0.13998(11) -0.13062(10) 0.02664(8) 0.0367(3) Uani 1 1 d . . . . .
O11 O 0.11737(11) 0.01809(10) 0.18870(8) 0.0369(3) Uani 1 1 d . . . . .
C1 C 0.2609(2) -0.26658(16) 0.14147(14) 0.0454(5) Uani 1 1 d . . . . .
H1A H 0.217904 -0.334602 0.100790 0.054 Uiso 1 1 calc R U . . .
H1B H 0.352321 -0.290391 0.169912 0.054 Uiso 1 1 calc R U . . .
C3 C 0.2399(2) -0.14028(17) 0.28137(13) 0.0447(5) Uani 1 1 d . . . . .
H3A H 0.330475 -0.161600 0.313293 0.054 Uiso 1 1 calc R U . . .
H3B H 0.182739 -0.125448 0.331673 0.054 Uiso 1 1 calc R U . . .
C3A C 0.25148(16) -0.02631(15) 0.22870(12) 0.0329(4) Uani 1 1 d . . . . .
C4 C 0.30848(17) 0.08740(16) 0.29179(12) 0.0358(4) Uani 1 1 d . . . . .
H4A H 0.256116 0.093990 0.346416 0.043 Uiso 1 1 calc R U . . .
C5 C 0.25691(16) 0.19021(15) 0.22330(12) 0.0363(4) Uani 1 1 d . . . . .
H5A H 0.198239 0.244017 0.256453 0.044 Uiso 1 1 calc R U . . .
C6A C 0.25765(16) 0.05400(14) 0.07102(11) 0.0310(4) Uani 1 1 d . . . . .
H6AA H 0.326550 0.109678 0.053287 0.037 Uiso 1 1 calc R U . . .
C6 C 0.16523(17) 0.11557(15) 0.13767(12) 0.0348(4) Uani 1 1 d . . . . .
H6A H 0.091106 0.162219 0.102567 0.042 Uiso 1 1 calc R U . . .
C7 C 0.18626(18) -0.02527(15) -0.01726(12) 0.0365(4) Uani 1 1 d . . . . .
H7A H 0.113236 0.015486 -0.058975 0.044 Uiso 1 1 calc R U . . .
C8 C 0.2980(2) -0.07886(17) -0.07187(13) 0.0458(5) Uani 1 1 d . . . . .
H8A H 0.368069 -0.018747 -0.077808 0.055 Uiso 1 1 calc R U . . .
H8B H 0.259109 -0.111978 -0.136488 0.055 Uiso 1 1 calc R U . . .
C9B C 0.32247(16) -0.04436(14) 0.13795(11) 0.0292(3) Uani 1 1 d . . . . .
H9BA H 0.422849 -0.037044 0.153090 0.035 Uiso 1 1 calc R U . . .
C9A C 0.27289(17) -0.16178(15) 0.07873(12) 0.0343(4) Uani 1 1 d . . . . .
C9 C 0.35641(19) -0.17935(16) -0.00495(13) 0.0429(4) Uani 1 1 d . . . . .
H9A H 0.340272 -0.258915 -0.037667 0.052 Uiso 1 1 calc R U . . .
H9B H 0.454044 -0.167261 0.017687 0.052 Uiso 1 1 calc R U . . .
C11 C 0.45794(19) 0.08944(17) 0.33680(12) 0.0399(4) Uani 1 1 d . . . . .
C12 C 0.6290(3) 0.2093(3) 0.4358(2) 0.0928(9) Uani 1 1 d . . . . .
H12A H 0.639162 0.282959 0.476137 0.139 Uiso 1 1 calc R U . . .
H12B H 0.660359 0.142808 0.474542 0.139 Uiso 1 1 calc R U . . .
H12C H 0.682464 0.215175 0.383838 0.139 Uiso 1 1 calc R U . . .
C13 C 0.36593(18) 0.26437(15) 0.18841(13) 0.0369(4) Uani 1 1 d . . . . .
C14 C 0.4051(2) 0.43334(18) 0.09688(16) 0.0559(5) Uani 1 1 d . . . . .
H14A H 0.355883 0.499566 0.066915 0.084 Uiso 1 1 calc R U . . .
H14B H 0.479391 0.464171 0.145224 0.084 Uiso 1 1 calc R U . . .
H14C H 0.441072 0.384269 0.047918 0.084 Uiso 1 1 calc R U . . .
O22 O 0.25756(14) 0.22500(13) 0.88132(9) 0.0541(4) Uani 1 1 d . . . . .
O23 O -0.01686(15) 0.21246(14) 0.57172(11) 0.0649(4) Uani 1 1 d . . . . .
O24 O 0.10626(14) 0.14250(13) 0.46090(10) 0.0572(4) Uani 1 1 d . . . . .
O25 O 0.11266(16) 0.40148(16) 0.44515(12) 0.0764(5) Uani 1 1 d . . . . .
O26 O 0.31694(14) 0.48846(12) 0.44806(10) 0.0538(4) Uani 1 1 d . . . . .
O30 O 0.26621(12) 0.49148(11) 0.86000(8) 0.0419(3) Uani 1 1 d . . . . .
O31 O 0.37354(12) 0.33903(11) 0.72942(9) 0.0440(3) Uani 1 1 d . . . . .
C21 C 0.1512(2) 0.30594(18) 0.89911(13) 0.0481(5) Uani 1 1 d . . . . .
H21A H 0.166639 0.333753 0.967485 0.058 Uiso 1 1 calc R U . . .
H21B H 0.063585 0.262801 0.886161 0.058 Uiso 1 1 calc R U . . .
C23A C 0.24119(18) 0.27653(16) 0.71240(13) 0.0386(4) Uani 1 1 d . . . . .
C23 C 0.2392(2) 0.17763(18) 0.78274(14) 0.0528(5) Uani 1 1 d . . . . .
H23A H 0.152118 0.133728 0.768047 0.063 Uiso 1 1 calc R U . . .
H23B H 0.311816 0.121248 0.774520 0.063 Uiso 1 1 calc R U . . .
C24 C 0.23219(18) 0.23790(16) 0.60227(12) 0.0389(4) Uani 1 1 d . . . . .
H24A H 0.292657 0.168690 0.598041 0.047 Uiso 1 1 calc R U . . .
C25 C 0.30505(17) 0.34876(16) 0.56478(12) 0.0386(4) Uani 1 1 d . . . . .
H25A H 0.392213 0.320677 0.546644 0.046 Uiso 1 1 calc R U . . .
C26 C 0.33967(17) 0.43013(16) 0.66067(12) 0.0387(4) Uani 1 1 d . . . . .
H26A H 0.414921 0.488264 0.659355 0.046 Uiso 1 1 calc R U . . .
C26A C 0.21025(17) 0.48841(15) 0.68991(12) 0.0347(4) Uani 1 1 d . . . . .
H26B H 0.152280 0.523357 0.634779 0.042 Uiso 1 1 calc R U . . .
C27 C 0.22982(19) 0.57283(16) 0.78273(13) 0.0405(4) Uani 1 1 d . . . . .
H27A H 0.297314 0.638290 0.782171 0.049 Uiso 1 1 calc R U . . .
C28 C 0.0882(2) 0.61675(17) 0.80254(15) 0.0482(5) Uani 1 1 d . . . . .
H28A H 0.096955 0.686747 0.848263 0.058 Uiso 1 1 calc R U . . .
H28B H 0.029940 0.636358 0.742584 0.058 Uiso 1 1 calc R U . . .
C29B C 0.14132(17) 0.37783(15) 0.72763(11) 0.0324(4) Uani 1 1 d . . . . .
H29C H 0.048131 0.360650 0.692953 0.039 Uiso 1 1 calc R U . . .
C29A C 0.14461(17) 0.41387(16) 0.83682(12) 0.0369(4) Uani 1 1 d . . . . .
C29 C 0.03214(19) 0.50545(18) 0.84699(14) 0.0465(5) Uani 1 1 d . . . . .
H29A H 0.022446 0.522262 0.914929 0.056 Uiso 1 1 calc R U . . .
H29B H -0.055661 0.477811 0.810518 0.056 Uiso 1 1 calc R U . . .
C31 C 0.0927(2) 0.20012(16) 0.54613(13) 0.0410(4) Uani 1 1 d . . . . .
C32 C -0.0213(2) 0.1150(2) 0.39570(15) 0.0597(6) Uani 1 1 d . . . . .
H32A H -0.001721 0.073977 0.336819 0.090 Uiso 1 1 calc R U . . .
H32B H -0.078545 0.064075 0.427133 0.090 Uiso 1 1 calc R U . . .
H32C H -0.068036 0.188754 0.379963 0.090 Uiso 1 1 calc R U . . .
C33 C 0.23067(19) 0.41230(17) 0.47975(13) 0.0396(4) Uani 1 1 d . . . . .
C34 C 0.2618(2) 0.5574(2) 0.36618(15) 0.0628(6) Uani 1 1 d . . . . .
H34A H 0.332648 0.609042 0.349670 0.094 Uiso 1 1 calc R U . . .
H34B H 0.228085 0.503362 0.311133 0.094 Uiso 1 1 calc R U . . .
H34C H 0.187780 0.605899 0.383169 0.094 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C3 1.424(2) . ?
O2 C1 1.426(2) . ?
O3 C11 1.193(2) . ?
O4 C11 1.342(2) . ?
O4 C12 1.438(3) . ?
O5 C13 1.204(2) . ?
O6 C13 1.334(2) . ?
O6 C14 1.461(2) . ?
O10 C7 1.4454(19) . ?
O10 C9A 1.4480(19) . ?
O11 C6 1.436(2) . ?
O11 C3A 1.4520(19) . ?
C1 C9A 1.501(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 C3A 1.503(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3A C9B 1.536(2) . ?
C3A C4 1.545(2) . ?
C4 C11 1.507(2) . ?
C4 C5 1.559(2) . ?
C4 H4A 0.9800 . ?
C5 C13 1.499(2) . ?
C5 C6 1.569(2) . ?
C5 H5A 0.9800 . ?
C6A C6 1.534(2) . ?
C6A C7 1.541(2) . ?
C6A C9B 1.546(2) . ?
C6A H6AA 0.9800 . ?
C6 H6A 0.9800 . ?
C7 C8 1.536(2) . ?
C7 H7A 0.9800 . ?
C8 C9 1.545(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9B C9A 1.535(2) . ?
C9B H9BA 0.9800 . ?
C9A C9 1.528(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O22 C23 1.422(2) . ?
O22 C21 1.427(2) . ?
O23 C31 1.194(2) . ?
O24 C31 1.339(2) . ?
O24 C32 1.449(2) . ?
O25 C33 1.189(2) . ?
O26 C33 1.329(2) . ?
O26 C34 1.441(2) . ?
O30 C27 1.441(2) . ?
O30 C29A 1.452(2) . ?
O31 C26 1.430(2) . ?
O31 C23A 1.451(2) . ?
C21 C29A 1.507(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C23A C23 1.506(2) . ?
C23A C29B 1.527(2) . ?
C23A C24 1.553(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C31 1.514(3) . ?
C24 C25 1.568(2) . ?
C24 H24A 0.9800 . ?
C25 C33 1.500(2) . ?
C25 C26 1.557(2) . ?
C25 H25A 0.9800 . ?
C26 C26A 1.534(2) . ?
C26 H26A 0.9800 . ?
C26A C27 1.537(2) . ?
C26A C29B 1.548(2) . ?
C26A H26B 0.9800 . ?
C27 C28 1.541(3) . ?
C27 H27A 0.9800 . ?
C28 C29 1.541(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29B C29A 1.541(2) . ?
C29B H29C 0.9800 . ?
C29A C29 1.527(2) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?

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
C3 O2 C1 112.45(13) . . ?
C11 O4 C12 115.59(17) . . ?
C13 O6 C14 116.43(14) . . ?
C7 O10 C9A 96.63(12) . . ?
C6 O11 C3A 97.10(11) . . ?
O2 C1 C9A 112.74(14) . . ?
O2 C1 H1A 109.0 . . ?
C9A C1 H1A 109.0 . . ?
O2 C1 H1B 109.0 . . ?
C9A C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
O2 C3 C3A 112.83(14) . . ?
O2 C3 H3A 109.0 . . ?
C3A C3 H3A 109.0 . . ?
O2 C3 H3B 109.0 . . ?
C3A C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
O11 C3A C3 111.68(13) . . ?
O11 C3A C9B 102.95(12) . . ?
C3 C3A C9B 113.34(14) . . ?
O11 C3A C4 99.07(12) . . ?
C3 C3A C4 116.75(14) . . ?
C9B C3A C4 111.27(13) . . ?
C11 C4 C3A 117.86(14) . . ?
C11 C4 C5 117.95(14) . . ?
C3A C4 C5 101.48(13) . . ?
C11 C4 H4A 106.2 . . ?
C3A C4 H4A 106.2 . . ?
C5 C4 H4A 106.2 . . ?
C13 C5 C4 116.17(14) . . ?
C13 C5 C6 112.49(14) . . ?
C4 C5 C6 100.71(13) . . ?
C13 C5 H5A 109.0 . . ?
C4 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
C6 C6A C7 117.16(14) . . ?
C6 C6A C9B 100.22(12) . . ?
C7 C6A C9B 100.54(12) . . ?
C6 C6A H6AA 112.5 . . ?
C7 C6A H6AA 112.5 . . ?
C9B C6A H6AA 112.5 . . ?
O11 C6 C6A 104.02(12) . . ?
O11 C6 C5 101.29(13) . . ?
C6A C6 C5 109.33(13) . . ?
O11 C6 H6A 113.7 . . ?
C6A C6 H6A 113.7 . . ?
C5 C6 H6A 113.7 . . ?
O10 C7 C8 101.53(13) . . ?
O10 C7 C6A 103.54(12) . . ?
C8 C7 C6A 108.04(14) . . ?
O10 C7 H7A 114.2 . . ?
C8 C7 H7A 114.2 . . ?
C6A C7 H7A 114.2 . . ?
C7 C8 C9 102.18(14) . . ?
C7 C8 H8A 111.3 . . ?
C9 C8 H8A 111.3 . . ?
C7 C8 H8B 111.3 . . ?
C9 C8 H8B 111.3 . . ?
H8A C8 H8B 109.2 . . ?
C9A C9B C3A 111.37(13) . . ?
C9A C9B C6A 102.48(12) . . ?
C3A C9B C6A 102.97(12) . . ?
C9A C9B H9BA 113.0 . . ?
C3A C9B H9BA 113.0 . . ?
C6A C9B H9BA 113.0 . . ?
O10 C9A C1 111.19(14) . . ?
O10 C9A C9 101.48(13) . . ?
C1 C9A C9 117.65(14) . . ?
O10 C9A C9B 103.37(12) . . ?
C1 C9A C9B 113.15(14) . . ?
C9 C9A C9B 108.48(14) . . ?
C9A C9 C8 100.97(14) . . ?
C9A C9 H9A 111.6 . . ?
C8 C9 H9A 111.6 . . ?
C9A C9 H9B 111.6 . . ?
C8 C9 H9B 111.6 . . ?
H9A C9 H9B 109.4 . . ?
O3 C11 O4 123.27(17) . . ?
O3 C11 C4 126.94(17) . . ?
O4 C11 C4 109.67(15) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 O6 123.17(17) . . ?
O5 C13 C5 125.79(16) . . ?
O6 C13 C5 110.95(15) . . ?
O6 C14 H14A 109.5 . . ?
O6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C23 O22 C21 112.15(14) . . ?
C31 O24 C32 115.26(15) . . ?
C33 O26 C34 116.66(16) . . ?
C27 O30 C29A 96.65(12) . . ?
C26 O31 C23A 97.04(12) . . ?
O22 C21 C29A 112.63(15) . . ?
O22 C21 H21A 109.1 . . ?
C29A C21 H21A 109.1 . . ?
O22 C21 H21B 109.1 . . ?
C29A C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
O31 C23A C23 110.28(15) . . ?
O31 C23A C29B 102.81(14) . . ?
C23 C23A C29B 113.31(15) . . ?
O31 C23A C24 100.10(13) . . ?
C23 C23A C24 117.40(15) . . ?
C29B C23A C24 111.09(14) . . ?
O22 C23 C23A 111.50(16) . . ?
O22 C23 H23A 109.3 . . ?
C23A C23 H23A 109.3 . . ?
O22 C23 H23B 109.3 . . ?
C23A C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
C31 C24 C23A 117.84(14) . . ?
C31 C24 C25 116.56(14) . . ?
C23A C24 C25 100.82(14) . . ?
C31 C24 H24A 107.0 . . ?
C23A C24 H24A 107.0 . . ?
C25 C24 H24A 107.0 . . ?
C33 C25 C26 114.25(14) . . ?
C33 C25 C24 118.47(15) . . ?
C26 C25 C24 101.08(13) . . ?
C33 C25 H25A 107.5 . . ?
C26 C25 H25A 107.5 . . ?
C24 C25 H25A 107.5 . . ?
O31 C26 C26A 104.48(13) . . ?
O31 C26 C25 99.78(13) . . ?
C26A C26 C25 111.40(14) . . ?
O31 C26 H26A 113.4 . . ?
C26A C26 H26A 113.4 . . ?
C25 C26 H26A 113.4 . . ?
C26 C26A C27 116.94(14) . . ?
C26 C26A C29B 100.43(13) . . ?
C27 C26A C29B 100.13(13) . . ?
C26 C26A H26B 112.6 . . ?
C27 C26A H26B 112.6 . . ?
C29B C26A H26B 112.6 . . ?
O30 C27 C26A 103.28(13) . . ?
O30 C27 C28 101.87(14) . . ?
C26A C27 C28 109.07(14) . . ?
O30 C27 H27A 113.8 . . ?
C26A C27 H27A 113.8 . . ?
C28 C27 H27A 113.8 . . ?
C29 C28 C27 101.74(15) . . ?
C29 C28 H28A 111.4 . . ?
C27 C28 H28A 111.4 . . ?
C29 C28 H28B 111.4 . . ?
C27 C28 H28B 111.4 . . ?
H28A C28 H28B 109.3 . . ?
C23A C29B C29A 111.83(14) . . ?
C23A C29B C26A 102.61(13) . . ?
C29A C29B C26A 102.74(13) . . ?
C23A C29B H29C 112.9 . . ?
C29A C29B H29C 112.9 . . ?
C26A C29B H29C 112.9 . . ?
O30 C29A C21 112.58(14) . . ?
O30 C29A C29 100.55(14) . . ?
C21 C29A C29 117.63(15) . . ?
O30 C29A C29B 103.11(13) . . ?
C21 C29A C29B 112.52(14) . . ?
C29 C29A C29B 108.89(14) . . ?
C29A C29 C28 101.43(14) . . ?
C29A C29 H29A 111.5 . . ?
C28 C29 H29A 111.5 . . ?
C29A C29 H29B 111.5 . . ?
C28 C29 H29B 111.5 . . ?
H29A C29 H29B 109.3 . . ?
O23 C31 O24 121.76(18) . . ?
O23 C31 C24 127.70(17) . . ?
O24 C31 C24 110.47(15) . . ?
O24 C32 H32A 109.5 . . ?
O24 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O24 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O25 C33 O26 123.17(17) . . ?
O25 C33 C25 127.41(17) . . ?
O26 C33 C25 109.40(15) . . ?
O26 C34 H34A 109.5 . . ?
O26 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O26 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 O2 C1 C9A -58.98(19) . . . . ?
C1 O2 C3 C3A 58.51(19) . . . . ?
C6 O11 C3A C3 -174.71(13) . . . . ?
C6 O11 C3A C9B -52.79(14) . . . . ?
C6 O11 C3A C4 61.65(13) . . . . ?
O2 C3 C3A O11 65.30(18) . . . . ?
O2 C3 C3A C9B -50.4(2) . . . . ?
O2 C3 C3A C4 178.27(14) . . . . ?
O11 C3A C4 C11 -170.96(13) . . . . ?
C3 C3A C4 C11 69.1(2) . . . . ?
C9B C3A C4 C11 -63.16(19) . . . . ?
O11 C3A C4 C5 -40.53(14) . . . . ?
C3 C3A C4 C5 -160.49(14) . . . . ?
C9B C3A C4 C5 67.27(15) . . . . ?
C11 C4 C5 C13 14.6(2) . . . . ?
C3A C4 C5 C13 -115.74(15) . . . . ?
C11 C4 C5 C6 136.40(14) . . . . ?
C3A C4 C5 C6 6.04(14) . . . . ?
C3A O11 C6 C6A 55.62(14) . . . . ?
C3A O11 C6 C5 -57.82(13) . . . . ?
C7 C6A C6 O11 71.75(16) . . . . ?
C9B C6A C6 O11 -35.80(15) . . . . ?
C7 C6A C6 C5 179.30(13) . . . . ?
C9B C6A C6 C5 71.75(15) . . . . ?
C13 C5 C6 O11 155.14(13) . . . . ?
C4 C5 C6 O11 30.81(14) . . . . ?
C13 C5 C6 C6A 45.76(18) . . . . ?
C4 C5 C6 C6A -78.57(15) . . . . ?
C9A O10 C7 C8 56.35(14) . . . . ?
C9A O10 C7 C6A -55.63(14) . . . . ?
C6 C6A C7 O10 -71.88(17) . . . . ?
C9B C6A C7 O10 35.48(15) . . . . ?
C6 C6A C7 C8 -179.02(14) . . . . ?
C9B C6A C7 C8 -71.66(15) . . . . ?
O10 C7 C8 C9 -32.67(16) . . . . ?
C6A C7 C8 C9 75.86(16) . . . . ?
O11 C3A C9B C9A -78.52(15) . . . . ?
C3 C3A C9B C9A 42.29(19) . . . . ?
C4 C3A C9B C9A 176.23(13) . . . . ?
O11 C3A C9B C6A 30.65(15) . . . . ?
C3 C3A C9B C6A 151.45(14) . . . . ?
C4 C3A C9B C6A -74.60(15) . . . . ?
C6 C6A C9B C9A 118.31(13) . . . . ?
C7 C6A C9B C9A -2.05(15) . . . . ?
C6 C6A C9B C3A 2.59(15) . . . . ?
C7 C6A C9B C3A -117.77(13) . . . . ?
C7 O10 C9A C1 175.47(13) . . . . ?
C7 O10 C9A C9 -58.62(14) . . . . ?
C7 O10 C9A C9B 53.76(14) . . . . ?
O2 C1 C9A O10 -64.58(19) . . . . ?
O2 C1 C9A C9 179.06(15) . . . . ?
O2 C1 C9A C9B 51.2(2) . . . . ?
C3A C9B C9A O10 77.71(15) . . . . ?
C6A C9B C9A O10 -31.76(15) . . . . ?
C3A C9B C9A C1 -42.67(19) . . . . ?
C6A C9B C9A C1 -152.14(14) . . . . ?
C3A C9B C9A C9 -175.13(13) . . . . ?
C6A C9B C9A C9 75.40(16) . . . . ?
O10 C9A C9 C8 37.16(16) . . . . ?
C1 C9A C9 C8 158.68(15) . . . . ?
C9B C9A C9 C8 -71.30(16) . . . . ?
C7 C8 C9 C9A -2.63(17) . . . . ?
C12 O4 C11 O3 9.5(3) . . . . ?
C12 O4 C11 C4 -174.39(19) . . . . ?
C3A C4 C11 O3 0.9(3) . . . . ?
C5 C4 C11 O3 -121.5(2) . . . . ?
C3A C4 C11 O4 -175.04(15) . . . . ?
C5 C4 C11 O4 62.58(19) . . . . ?
C14 O6 C13 O5 2.9(2) . . . . ?
C14 O6 C13 C5 -173.81(15) . . . . ?
C4 C5 C13 O5 13.1(2) . . . . ?
C6 C5 C13 O5 -102.3(2) . . . . ?
C4 C5 C13 O6 -170.36(13) . . . . ?
C6 C5 C13 O6 74.33(17) . . . . ?
C23 O22 C21 C29A -60.5(2) . . . . ?
C26 O31 C23A C23 -175.12(14) . . . . ?
C26 O31 C23A C29B -54.01(14) . . . . ?
C26 O31 C23A C24 60.53(14) . . . . ?
C21 O22 C23 C23A 60.9(2) . . . . ?
O31 C23A C23 O22 62.3(2) . . . . ?
C29B C23A C23 O22 -52.4(2) . . . . ?
C24 C23A C23 O22 175.97(15) . . . . ?
O31 C23A C24 C31 -163.09(14) . . . . ?
C23 C23A C24 C31 77.6(2) . . . . ?
C29B C23A C24 C31 -55.0(2) . . . . ?
O31 C23A C24 C25 -35.09(15) . . . . ?
C23 C23A C24 C25 -154.36(16) . . . . ?
C29B C23A C24 C25 72.98(16) . . . . ?
C31 C24 C25 C33 2.4(2) . . . . ?
C23A C24 C25 C33 -126.40(16) . . . . ?
C31 C24 C25 C26 128.05(15) . . . . ?
C23A C24 C25 C26 -0.78(15) . . . . ?
C23A O31 C26 C26A 54.42(15) . . . . ?
C23A O31 C26 C25 -60.85(14) . . . . ?
C33 C25 C26 O31 165.38(14) . . . . ?
C24 C25 C26 O31 36.98(14) . . . . ?
C33 C25 C26 C26A 55.50(19) . . . . ?
C24 C25 C26 C26A -72.89(16) . . . . ?
O31 C26 C26A C27 74.04(17) . . . . ?
C25 C26 C26A C27 -179.12(14) . . . . ?
O31 C26 C26A C29B -33.07(16) . . . . ?
C25 C26 C26A C29B 73.77(15) . . . . ?
C29A O30 C27 C26A -57.03(15) . . . . ?
C29A O30 C27 C28 56.10(15) . . . . ?
C26 C26A C27 O30 -69.36(17) . . . . ?
C29B C26A C27 O30 37.92(15) . . . . ?
C26 C26A C27 C28 -177.13(14) . . . . ?
C29B C26A C27 C28 -69.85(16) . . . . ?
O30 C27 C28 C29 -31.17(16) . . . . ?
C26A C27 C28 C29 77.56(16) . . . . ?
O31 C23A C29B C29A -76.00(16) . . . . ?
C23 C23A C29B C29A 43.0(2) . . . . ?
C24 C23A C29B C29A 177.71(13) . . . . ?
O31 C23A C29B C26A 33.45(15) . . . . ?
C23 C23A C29B C26A 152.47(15) . . . . ?
C24 C23A C29B C26A -72.84(16) . . . . ?
C26 C26A C29B C23A -0.66(16) . . . . ?
C27 C26A C29B C23A -120.72(14) . . . . ?
C26 C26A C29B C29A 115.52(14) . . . . ?
C27 C26A C29B C29A -4.53(15) . . . . ?
C27 O30 C29A C21 174.58(14) . . . . ?
C27 O30 C29A C29 -59.37(14) . . . . ?
C27 O30 C29A C29B 53.06(14) . . . . ?
O22 C21 C29A O30 -65.53(19) . . . . ?
O22 C21 C29A C29 178.27(15) . . . . ?
O22 C21 C29A C29B 50.5(2) . . . . ?
C23A C29B C29A O30 79.77(16) . . . . ?
C26A C29B C29A O30 -29.60(16) . . . . ?
C23A C29B C29A C21 -41.8(2) . . . . ?
C26A C29B C29A C21 -151.16(14) . . . . ?
C23A C29B C29A C29 -174.06(14) . . . . ?
C26A C29B C29A C29 76.57(16) . . . . ?
O30 C29A C29 C28 38.90(16) . . . . ?
C21 C29A C29 C28 161.47(15) . . . . ?
C29B C29A C29 C28 -69.02(17) . . . . ?
C27 C28 C29 C29A -4.75(17) . . . . ?
C32 O24 C31 O23 10.0(3) . . . . ?
C32 O24 C31 C24 -172.85(15) . . . . ?
C23A C24 C31 O23 11.9(3) . . . . ?
C25 C24 C31 O23 -108.1(2) . . . . ?
C23A C24 C31 O24 -164.99(15) . . . . ?
C25 C24 C31 O24 74.92(19) . . . . ?
C34 O26 C33 O25 -1.6(3) . . . . ?
C34 O26 C33 C25 -179.92(16) . . . . ?
C26 C25 C33 O25 -106.2(2) . . . . ?
C24 C25 C33 O25 12.7(3) . . . . ?
C26 C25 C33 O26 72.04(18) . . . . ?
C24 C25 C33 O26 -169.00(14) . . . . ?

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
C3 H3B O23 0.97 2.48 3.336(2) 146.4 2_556 yes
C4 H4A O24 0.98 2.37 3.339(2) 168.3 . yes
C9B H9BA O3 0.98 2.55 3.161(2) 120.3 . yes
C14 H14B O30 0.96 2.56 3.291(2) 132.9 2_666 yes
C27 H27A O5 0.98 2.49 3.436(2) 163.2 2_666 yes
C29B H29C O23 0.98 2.30 2.991(2) 126.8 . yes
C32 H32A O11 0.96 2.57 3.489(2) 160.4 . yes

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.044



# start Validation Reply Form
_vrf_PLAT910_9a                  
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 24 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_XB6544
_database_code_depnum_ccdc_archive 'CCDC 2095412'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2021-07-09 deposited with the CCDC.	2021-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 O9'
_chemical_formula_sum            'C16 H16 O9'
_chemical_formula_weight         352.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 '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'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.4396(19)
_cell_length_b                   11.620(2)
_cell_length_c                   13.907(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.59(3)
_cell_angle_gamma                90
_cell_volume                     1524.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      3.6
_cell_measurement_theta_max      36.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.277
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_process_details   'Scala (Evans, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96990
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38143
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.607
_diffrn_reflns_theta_max         38.488
_diffrn_reflns_theta_full        35.587
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3290
_reflns_number_gt                2746
_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       Automar
_computing_cell_refinement       iMosflm
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0756P)²+1.23P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3290
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1469
_refine_ls_wR_factor_gt          0.1419
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.6684(2) 0.31622(18) 0.74444(14) 0.0235(4) Uani 1 1 d . . . . .
H1A H 0.5976 0.3139 0.7956 0.028 Uiso 1 1 calc R U . . .
H1B H 0.7501 0.2680 0.7654 0.028 Uiso 1 1 calc R U . . .
O2 O 0.71463(15) 0.43177(12) 0.73144(9) 0.0238(3) Uani 1 1 d . . . . .
O3 O 0.86526(15) 0.50542(12) 0.42574(9) 0.0222(3) Uani 1 1 d . . . . .
O4 O 0.66184(13) 0.46845(11) 0.52835(9) 0.0175(3) Uani 1 1 d . . . . .
O5 O 0.48636(14) 0.33723(11) 0.61942(9) 0.0186(3) Uani 1 1 d . . . . .
O6 O 0.38573(15) 0.15024(12) 0.66611(10) 0.0239(3) Uani 1 1 d . . . . .
O7 O 0.48652(16) 0.15151(13) 0.36364(10) 0.0274(4) Uani 1 1 d . . . . .
O8 O 0.71975(14) 0.18674(11) 0.35332(9) 0.0206(3) Uani 1 1 d . . . . .
O9 O 0.77793(15) 0.07754(12) 0.53245(10) 0.0235(3) Uani 1 1 d . . . . .
O10 O 0.92901(15) 0.19744(12) 0.61106(11) 0.0248(3) Uani 1 1 d . . . . .
C3 C 0.8256(2) 0.44029(17) 0.66295(13) 0.0211(4) Uani 1 1 d . . . . .
H3A H 0.9082 0.3944 0.6858 0.025 Uiso 1 1 calc R U . . .
H3B H 0.8560 0.5215 0.6578 0.025 Uiso 1 1 calc R U . . .
C3A C 0.7759(2) 0.39721(16) 0.56459(13) 0.0173(4) Uani 1 1 d . . . . .
C4 C 0.8771(2) 0.39923(16) 0.47936(13) 0.0183(4) Uani 1 1 d . . . . .
H4 H 0.9646 0.3507 0.4786 0.022 Uiso 1 1 calc R U . . .
C5 C 0.7796(2) 0.40779(15) 0.39533(13) 0.0180(4) Uani 1 1 d . . . . .
H5 H 0.7978 0.3656 0.3342 0.022 Uiso 1 1 calc R U . . .
C6 C 0.6312(2) 0.40922(15) 0.43969(13) 0.0171(4) Uani 1 1 d . . . . .
H6 H 0.5553 0.4455 0.3982 0.020 Uiso 1 1 calc R U . . .
C6A C 0.5951(2) 0.28415(15) 0.47664(13) 0.0163(4) Uani 1 1 d . . . . .
C7 C 0.4512(2) 0.27792(16) 0.53110(13) 0.0178(4) Uani 1 1 d . . . . .
H7 H 0.3672 0.3094 0.4945 0.021 Uiso 1 1 calc R U . . .
C8 C 0.4341(2) 0.15346(17) 0.56755(14) 0.0208(4) Uani 1 1 d . . . . .
H8 H 0.4181 0.0875 0.5223 0.025 Uiso 1 1 calc R U . . .
C9 C 0.5362(2) 0.14618(16) 0.64964(13) 0.0206(4) Uani 1 1 d . . . . .
H9 H 0.5937 0.0754 0.6628 0.025 Uiso 1 1 calc R U . . .
C9A C 0.6029(2) 0.26735(16) 0.65163(12) 0.0179(4) Uani 1 1 d . . . . .
C9B C 0.7055(2) 0.27465(15) 0.56380(12) 0.0160(4) Uani 1 1 d . . . . .
C10 C 0.5941(2) 0.19782(16) 0.39360(13) 0.0172(4) Uani 1 1 d . . . . .
C11 C 0.7221(2) 0.11410(18) 0.26795(14) 0.0239(4) Uani 1 1 d . . . . .
H11A H 0.6570 0.1454 0.2185 0.036 Uiso 1 1 calc R U . . .
H11B H 0.6926 0.0359 0.2846 0.036 Uiso 1 1 calc R U . . .
H11C H 0.8184 0.1121 0.2434 0.036 Uiso 1 1 calc R U . . .
C12 C 0.8061(2) 0.17178(16) 0.56441(13) 0.0182(4) Uani 1 1 d . . . . .
C13 C 1.0278(2) 0.1024(2) 0.62520(19) 0.0332(5) Uani 1 1 d . . . . .
H13A H 1.0524 0.0705 0.5626 0.050 Uiso 1 1 calc R U . . .
H13B H 0.9837 0.0424 0.6639 0.050 Uiso 1 1 calc R U . . .
H13C H 1.1139 0.1302 0.6587 0.050 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.425(2) . ?
C1 C9A 1.525(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
O2 C3 1.438(2) . ?
O3 C4 1.444(2) . ?
O3 C5 1.449(2) . ?
O4 C6 1.435(2) . ?
O4 C3A 1.438(2) . ?
O5 C9A 1.429(2) . ?
O5 C7 1.439(2) . ?
O6 C9 1.445(2) . ?
O6 C8 1.457(2) . ?
O7 C10 1.213(2) . ?
O8 C10 1.332(2) . ?
O8 C11 1.457(2) . ?
O9 C12 1.209(2) . ?
O10 C12 1.347(2) . ?
O10 C13 1.455(2) . ?
C3 C3A 1.518(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4 1.543(3) . ?
C3A C9B 1.572(3) . ?
C4 C5 1.471(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.546(3) . ?
C5 H5 1.0000 . ?
C6 C6A 1.582(3) . ?
C6 H6 1.0000 . ?
C6A C10 1.529(2) . ?
C6A C7 1.575(2) . ?
C6A C9B 1.580(3) . ?
C7 C8 1.543(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.476(3) . ?
C8 H8 1.0000 . ?
C9 C9A 1.543(3) . ?
C9 H9 1.0000 . ?
C9A C9B 1.582(2) . ?
C9B C12 1.527(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 C9A 111.20(16) . . ?
O2 C1 H1A 109.4 . . ?
C9A C1 H1A 109.4 . . ?
O2 C1 H1B 109.4 . . ?
C9A C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C1 O2 C3 112.32(14) . . ?
C4 O3 C5 61.10(12) . . ?
C6 O4 C3A 98.98(13) . . ?
C9A O5 C7 98.78(13) . . ?
C9 O6 C8 61.12(12) . . ?
C10 O8 C11 115.63(15) . . ?
C12 O10 C13 115.93(16) . . ?
O2 C3 C3A 111.22(16) . . ?
O2 C3 H3A 109.4 . . ?
C3A C3 H3A 109.4 . . ?
O2 C3 H3B 109.4 . . ?
C3A C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
O4 C3A C3 109.58(15) . . ?
O4 C3A C4 101.29(14) . . ?
C3 C3A C4 120.32(16) . . ?
O4 C3A C9B 101.91(14) . . ?
C3 C3A C9B 115.14(15) . . ?
C4 C3A C9B 106.22(14) . . ?
O3 C4 C5 59.62(11) . . ?
O3 C4 C3A 111.63(15) . . ?
C5 C4 C3A 102.94(15) . . ?
O3 C4 H4 121.9 . . ?
C5 C4 H4 121.9 . . ?
C3A C4 H4 121.9 . . ?
O3 C5 C4 59.29(11) . . ?
O3 C5 C6 112.30(14) . . ?
C4 C5 C6 103.76(14) . . ?
O3 C5 H5 121.6 . . ?
C4 C5 H5 121.6 . . ?
C6 C5 H5 121.6 . . ?
O4 C6 C5 100.66(14) . . ?
O4 C6 C6A 101.63(13) . . ?
C5 C6 C6A 109.01(14) . . ?
O4 C6 H6 114.6 . . ?
C5 C6 H6 114.6 . . ?
C6A C6 H6 114.6 . . ?
C10 C6A C7 110.22(15) . . ?
C10 C6A C9B 121.56(15) . . ?
C7 C6A C9B 100.78(13) . . ?
C10 C6A C6 110.74(14) . . ?
C7 C6A C6 113.28(14) . . ?
C9B C6A C6 99.77(14) . . ?
O5 C7 C8 101.09(14) . . ?
O5 C7 C6A 101.95(14) . . ?
C8 C7 C6A 107.52(15) . . ?
O5 C7 H7 114.9 . . ?
C8 C7 H7 114.9 . . ?
C6A C7 H7 114.9 . . ?
O6 C8 C9 59.05(12) . . ?
O6 C8 C7 111.82(15) . . ?
C9 C8 C7 103.63(16) . . ?
O6 C8 H8 121.8 . . ?
C9 C8 H8 121.8 . . ?
C7 C8 H8 121.8 . . ?
O6 C9 C8 59.83(12) . . ?
O6 C9 C9A 111.72(15) . . ?
C8 C9 C9A 102.67(15) . . ?
O6 C9 H9 121.9 . . ?
C8 C9 H9 121.9 . . ?
C9A C9 H9 121.9 . . ?
O5 C9A C1 110.13(15) . . ?
O5 C9A C9 101.66(15) . . ?
C1 C9A C9 120.72(16) . . ?
O5 C9A C9B 102.11(13) . . ?
C1 C9A C9B 113.03(16) . . ?
C9 C9A C9B 107.07(14) . . ?
C12 C9B C3A 116.50(15) . . ?
C12 C9B C6A 117.13(15) . . ?
C3A C9B C6A 102.24(14) . . ?
C12 C9B C9A 110.35(14) . . ?
C3A C9B C9A 108.13(14) . . ?
C6A C9B C9A 101.03(14) . . ?
O7 C10 O8 124.02(16) . . ?
O7 C10 C6A 122.55(16) . . ?
O8 C10 C6A 113.21(15) . . ?
O8 C11 H11A 109.5 . . ?
O8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O9 C12 O10 123.76(18) . . ?
O9 C12 C9B 125.21(18) . . ?
O10 C12 C9B 110.91(15) . . ?
O10 C13 H13A 109.5 . . ?
O10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A C1 O2 C3 -63.4(2) . . . . ?
C1 O2 C3 C3A 60.7(2) . . . . ?
C6 O4 C3A C3 -177.86(14) . . . . ?
C6 O4 C3A C4 54.01(15) . . . . ?
C6 O4 C3A C9B -55.46(15) . . . . ?
O2 C3 C3A O4 62.80(19) . . . . ?
O2 C3 C3A C4 179.46(15) . . . . ?
O2 C3 C3A C9B -51.3(2) . . . . ?
C5 O3 C4 C3A -92.68(17) . . . . ?
O4 C3A C4 O3 29.77(18) . . . . ?
C3 C3A C4 O3 -91.1(2) . . . . ?
C9B C3A C4 O3 135.86(15) . . . . ?
O4 C3A C4 C5 -32.38(17) . . . . ?
C3 C3A C4 C5 -153.22(17) . . . . ?
C9B C3A C4 C5 73.72(17) . . . . ?
C4 O3 C5 C6 93.18(16) . . . . ?
C3A C4 C5 O3 107.68(15) . . . . ?
O3 C4 C5 C6 -107.99(15) . . . . ?
C3A C4 C5 C6 -0.30(17) . . . . ?
C3A O4 C6 C5 -53.81(15) . . . . ?
C3A O4 C6 C6A 58.34(15) . . . . ?
O3 C5 C6 O4 -29.18(18) . . . . ?
C4 C5 C6 O4 32.92(17) . . . . ?
O3 C5 C6 C6A -135.55(15) . . . . ?
C4 C5 C6 C6A -73.44(17) . . . . ?
O4 C6 C6A C10 -166.08(14) . . . . ?
C5 C6 C6A C10 -60.38(19) . . . . ?
O4 C6 C6A C7 69.49(18) . . . . ?
C5 C6 C6A C7 175.19(14) . . . . ?
O4 C6 C6A C9B -36.81(16) . . . . ?
C5 C6 C6A C9B 68.89(16) . . . . ?
C9A O5 C7 C8 53.42(16) . . . . ?
C9A O5 C7 C6A -57.37(15) . . . . ?
C10 C6A C7 O5 164.20(14) . . . . ?
C9B C6A C7 O5 34.56(16) . . . . ?
C6 C6A C7 O5 -71.10(18) . . . . ?
C10 C6A C7 C8 58.36(19) . . . . ?
C9B C6A C7 C8 -71.27(17) . . . . ?
C6 C6A C7 C8 -176.93(15) . . . . ?
C9 O6 C8 C7 -93.20(18) . . . . ?
O5 C7 C8 O6 29.70(19) . . . . ?
C6A C7 C8 O6 136.15(16) . . . . ?
O5 C7 C8 C9 -32.07(17) . . . . ?
C6A C7 C8 C9 74.38(17) . . . . ?
C8 O6 C9 C9A 92.38(16) . . . . ?
C7 C8 C9 O6 107.49(15) . . . . ?
O6 C8 C9 C9A -107.94(15) . . . . ?
C7 C8 C9 C9A -0.45(17) . . . . ?
C7 O5 C9A C1 176.77(14) . . . . ?
C7 O5 C9A C9 -54.09(15) . . . . ?
C7 O5 C9A C9B 56.45(15) . . . . ?
O2 C1 C9A O5 -58.0(2) . . . . ?
O2 C1 C9A C9 -175.92(16) . . . . ?
O2 C1 C9A C9B 55.5(2) . . . . ?
O6 C9 C9A O5 -29.12(18) . . . . ?
C8 C9 C9A O5 33.17(16) . . . . ?
O6 C9 C9A C1 93.0(2) . . . . ?
C8 C9 C9A C1 155.28(17) . . . . ?
O6 C9 C9A C9B -135.83(15) . . . . ?
C8 C9 C9A C9B -73.54(17) . . . . ?
O4 C3A C9B C12 159.49(14) . . . . ?
C3 C3A C9B C12 -82.0(2) . . . . ?
C4 C3A C9B C12 53.85(19) . . . . ?
O4 C3A C9B C6A 30.48(16) . . . . ?
C3 C3A C9B C6A 148.99(16) . . . . ?
C4 C3A C9B C6A -75.17(16) . . . . ?
O4 C3A C9B C9A -75.61(16) . . . . ?
C3 C3A C9B C9A 42.9(2) . . . . ?
C4 C3A C9B C9A 178.75(14) . . . . ?
C10 C6A C9B C12 -3.2(2) . . . . ?
C7 C6A C9B C12 118.77(16) . . . . ?
C6 C6A C9B C12 -125.06(16) . . . . ?
C10 C6A C9B C3A 125.39(17) . . . . ?
C7 C6A C9B C3A -112.61(14) . . . . ?
C6 C6A C9B C3A 3.56(15) . . . . ?
C10 C6A C9B C9A -123.10(17) . . . . ?
C7 C6A C9B C9A -1.10(16) . . . . ?
C6 C6A C9B C9A 115.07(14) . . . . ?
O5 C9A C9B C12 -157.50(15) . . . . ?
C1 C9A C9B C12 84.22(19) . . . . ?
C9 C9A C9B C12 -51.11(19) . . . . ?
O5 C9A C9B C3A 74.02(17) . . . . ?
C1 C9A C9B C3A -44.3(2) . . . . ?
C9 C9A C9B C3A -179.58(15) . . . . ?
O5 C9A C9B C6A -32.90(16) . . . . ?
C1 C9A C9B C6A -151.18(16) . . . . ?
C9 C9A C9B C6A 73.49(17) . . . . ?
C11 O8 C10 O7 0.3(3) . . . . ?
C11 O8 C10 C6A -174.30(16) . . . . ?
C7 C6A C10 O7 14.4(2) . . . . ?
C9B C6A C10 O7 131.83(19) . . . . ?
C6 C6A C10 O7 -111.7(2) . . . . ?
C7 C6A C10 O8 -170.84(15) . . . . ?
C9B C6A C10 O8 -53.4(2) . . . . ?
C6 C6A C10 O8 63.0(2) . . . . ?
C13 O10 C12 O9 -2.4(3) . . . . ?
C13 O10 C12 C9B 173.77(16) . . . . ?
C3A C9B C12 O9 -153.62(18) . . . . ?
C6A C9B C12 O9 -32.2(2) . . . . ?
C9A C9B C12 O9 82.6(2) . . . . ?
C3A C9B C12 O10 30.3(2) . . . . ?
C6A C9B C12 O10 151.73(15) . . . . ?
C9A C9B C12 O10 -93.47(17) . . . . ?

_refine_diff_density_max         0.535
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.069


####################################################################### 
# 
# 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_XB44
_database_code_depnum_ccdc_archive 'CCDC 2095413'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2021-07-09 deposited with the CCDC.	2021-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 O10 S'
_chemical_formula_sum            'C16 H16 O10 S'
_chemical_formula_weight         400.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 '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'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1970 0.2290 '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                   8.4936(17)
_cell_length_b                   16.170(3)
_cell_length_c                   11.847(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.38(3)
_cell_angle_gamma                90
_cell_volume                     1534.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    500
_cell_measurement_theta_min      3.5
_cell_measurement_theta_max      35.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.632
_shelx_estimated_absorpt_T_min   0.821
_shelx_estimated_absorpt_T_max   0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_process_details   'Scala (Evans, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96990
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22661
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.439
_diffrn_reflns_theta_max         38.567
_diffrn_reflns_theta_full        35.587
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measured_fraction_theta_full 0.949
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_Laue_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_point_group_measured_fraction_full 0.949
_reflns_number_total             3032
_reflns_number_gt                2173
_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       Automar
_computing_cell_refinement       iMosflm
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.08P)²+4P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0157(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3032
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.1783
_refine_ls_wR_factor_gt          0.1590
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2450(3) 0.38177(12) 0.60909(16) 0.0244(5) Uani 1 1 d . . . . .
O2 O 0.2629(3) 0.26347(12) 0.74442(16) 0.0275(5) Uani 1 1 d . . . . .
O3 O 0.5994(3) 0.58870(13) 0.89892(16) 0.0302(5) Uani 1 1 d . . . . .
O4 O 0.5137(2) 0.50686(11) 0.71253(14) 0.0188(4) Uani 1 1 d . . . . .
O5 O 0.5644(2) 0.40591(11) 0.55733(14) 0.0184(4) Uani 1 1 d . . . . .
O6 O 0.7285(3) 0.31430(13) 0.47398(17) 0.0324(6) Uani 1 1 d . . . . .
O7 O 1.0694(3) 0.46090(12) 0.82174(16) 0.0272(5) Uani 1 1 d . . . . .
O8 O 0.9934(2) 0.56778(12) 0.69368(16) 0.0240(5) Uani 1 1 d . . . . .
O9 O 0.8690(3) 0.37310(13) 0.97235(15) 0.0290(5) Uani 1 1 d . . . . .
O10 O 0.9363(2) 0.30096(11) 0.83394(15) 0.0214(5) Uani 1 1 d . . . . .
C1 C 0.5086(4) 0.28473(16) 0.6618(2) 0.0232(7) Uani 1 1 d . . . . .
H1A H 0.5660 0.2429 0.7225 0.028 Uiso 1 1 calc R U . . .
H1B H 0.4588 0.2555 0.5847 0.028 Uiso 1 1 calc R U . . .
S2 S 0.34451(9) 0.32955(4) 0.70371(5) 0.02218(17) Uani 1 1 d . . . . .
C3 C 0.4549(4) 0.39257(17) 0.8293(2) 0.0228(7) Uani 1 1 d . . . . .
H3A H 0.3734 0.4273 0.8512 0.027 Uiso 1 1 calc R U . . .
H3B H 0.5104 0.3562 0.8982 0.027 Uiso 1 1 calc R U . . .
C3A C 0.5860(4) 0.44877(16) 0.8069(2) 0.0195(6) Uani 1 1 d . . . . .
C4 C 0.6775(4) 0.50751(16) 0.9103(2) 0.0220(7) Uani 1 1 d . . . . .
H4 H 0.7501 0.4859 0.9895 0.026 Uiso 1 1 calc R U . . .
C5 C 0.7328(4) 0.57462(17) 0.8497(2) 0.0211(7) Uani 1 1 d . . . . .
H5 H 0.8450 0.6009 0.8852 0.025 Uiso 1 1 calc R U . . .
C6 C 0.6650(4) 0.55016(16) 0.7184(2) 0.0201(6) Uani 1 1 d . . . . .
H6 H 0.6489 0.5972 0.6610 0.024 Uiso 1 1 calc R U . . .
C6A C 0.7780(4) 0.47835(16) 0.6995(2) 0.0181(6) Uani 1 1 d . . . . .
C7 C 0.7147(3) 0.45013(16) 0.5645(2) 0.0191(6) Uani 1 1 d . . . . .
H7 H 0.6986 0.4962 0.5055 0.023 Uiso 1 1 calc R U . . .
C8 C 0.8279(4) 0.38048(17) 0.5499(2) 0.0212(7) Uani 1 1 d . . . . .
H8 H 0.9475 0.3901 0.5582 0.025 Uiso 1 1 calc R U . . .
C9 C 0.7748(4) 0.30931(17) 0.6036(2) 0.0209(6) Uani 1 1 d . . . . .
H9 H 0.8565 0.2673 0.6511 0.025 Uiso 1 1 calc R U . . .
C9A C 0.6377(4) 0.34558(15) 0.6487(2) 0.0193(6) Uani 1 1 d . . . . .
C9B C 0.7203(3) 0.40321(16) 0.7625(2) 0.0189(6) Uani 1 1 d . . . . .
C10 C 0.9615(4) 0.49964(16) 0.7460(2) 0.0193(6) Uani 1 1 d . . . . .
C11 C 1.1683(4) 0.59359(18) 0.7350(2) 0.0250(7) Uani 1 1 d . . . . .
H11A H 1.1787 0.6468 0.6983 0.037 Uiso 1 1 calc R U . . .
H11B H 1.2357 0.5519 0.7120 0.037 Uiso 1 1 calc R U . . .
H11C H 1.2077 0.5994 0.8222 0.037 Uiso 1 1 calc R U . . .
C12 C 0.8510(4) 0.35955(16) 0.8684(2) 0.0200(6) Uani 1 1 d . . . . .
C13 C 1.0727(4) 0.26410(18) 0.9283(2) 0.0237(7) Uani 1 1 d . . . . .
H13A H 1.1105 0.2141 0.8981 0.036 Uiso 1 1 calc R U . . .
H13B H 1.0350 0.2496 0.9955 0.036 Uiso 1 1 calc R U . . .
H13C H 1.1651 0.3036 0.9553 0.036 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 S2 1.4334(19) . ?
O2 S2 1.441(2) . ?
O3 C5 1.454(4) . ?
O3 C4 1.457(3) . ?
O4 C3A 1.433(3) . ?
O4 C6 1.445(3) . ?
O5 C9A 1.437(3) . ?
O5 C7 1.441(3) . ?
O6 C9 1.456(3) . ?
O6 C8 1.471(3) . ?
O7 C10 1.221(3) . ?
O8 C10 1.336(3) . ?
O8 C11 1.462(4) . ?
O9 C12 1.210(3) . ?
O10 C12 1.336(3) . ?
O10 C13 1.445(3) . ?
C1 C9A 1.519(4) . ?
C1 S2 1.781(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
S2 C3 1.790(3) . ?
C3 C3A 1.528(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4 1.541(3) . ?
C3A C9B 1.587(4) . ?
C4 C5 1.462(4) . ?
C4 H4 1.0000 . ?
C5 C6 1.520(3) . ?
C5 H5 1.0000 . ?
C6 C6A 1.569(4) . ?
C6 H6 1.0000 . ?
C6A C10 1.510(4) . ?
C6A C7 1.576(3) . ?
C6A C9B 1.586(4) . ?
C7 C8 1.527(4) . ?
C7 H7 1.0000 . ?
C8 C9 1.457(4) . ?
C8 H8 1.0000 . ?
C9 C9A 1.548(4) . ?
C9 H9 1.0000 . ?
C9A C9B 1.596(3) . ?
C9B C12 1.543(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O3 C4 60.30(18) . . ?
C3A O4 C6 97.80(19) . . ?
C9A O5 C7 97.95(19) . . ?
C9 O6 C8 59.72(17) . . ?
C10 O8 C11 114.9(2) . . ?
C12 O10 C13 115.64(19) . . ?
C9A C1 S2 115.02(19) . . ?
C9A C1 H1A 108.5 . . ?
S2 C1 H1A 108.5 . . ?
C9A C1 H1B 108.5 . . ?
S2 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
O1 S2 O2 118.31(13) . . ?
O1 S2 C1 109.52(13) . . ?
O2 S2 C1 107.42(13) . . ?
O1 S2 C3 108.95(12) . . ?
O2 S2 C3 108.75(12) . . ?
C1 S2 C3 102.77(14) . . ?
C3A C3 S2 113.92(19) . . ?
C3A C3 H3A 108.8 . . ?
S2 C3 H3A 108.8 . . ?
C3A C3 H3B 108.8 . . ?
S2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
O4 C3A C3 112.1(2) . . ?
O4 C3A C4 100.87(19) . . ?
C3 C3A C4 115.7(2) . . ?
O4 C3A C9B 102.4(2) . . ?
C3 C3A C9B 115.3(2) . . ?
C4 C3A C9B 108.8(2) . . ?
O3 C4 C5 59.77(18) . . ?
O3 C4 C3A 112.8(2) . . ?
C5 C4 C3A 103.1(2) . . ?
O3 C4 H4 121.5 . . ?
C5 C4 H4 121.5 . . ?
C3A C4 H4 121.5 . . ?
O3 C5 C4 59.93(18) . . ?
O3 C5 C6 111.7(2) . . ?
C4 C5 C6 103.6(2) . . ?
O3 C5 H5 121.7 . . ?
C4 C5 H5 121.7 . . ?
C6 C5 H5 121.7 . . ?
O4 C6 C5 101.8(2) . . ?
O4 C6 C6A 102.2(2) . . ?
C5 C6 C6A 107.2(2) . . ?
O4 C6 H6 114.7 . . ?
C5 C6 H6 114.7 . . ?
C6A C6 H6 114.7 . . ?
C10 C6A C6 112.7(2) . . ?
C10 C6A C7 113.5(2) . . ?
C6 C6A C7 109.9(2) . . ?
C10 C6A C9B 116.5(2) . . ?
C6 C6A C9B 101.6(2) . . ?
C7 C6A C9B 101.58(19) . . ?
O5 C7 C8 101.9(2) . . ?
O5 C7 C6A 101.6(2) . . ?
C8 C7 C6A 108.2(2) . . ?
O5 C7 H7 114.6 . . ?
C8 C7 H7 114.6 . . ?
C6A C7 H7 114.6 . . ?
C9 C8 O6 59.64(16) . . ?
C9 C8 C7 103.6(2) . . ?
O6 C8 C7 110.5(2) . . ?
C9 C8 H8 122.1 . . ?
O6 C8 H8 122.1 . . ?
C7 C8 H8 122.1 . . ?
O6 C9 C8 60.65(16) . . ?
O6 C9 C9A 111.9(2) . . ?
C8 C9 C9A 103.2(2) . . ?
O6 C9 H9 121.6 . . ?
C8 C9 H9 121.6 . . ?
C9A C9 H9 121.6 . . ?
O5 C9A C1 111.7(2) . . ?
O5 C9A C9 100.6(2) . . ?
C1 C9A C9 116.1(2) . . ?
O5 C9A C9B 101.48(18) . . ?
C1 C9A C9B 115.0(2) . . ?
C9 C9A C9B 110.0(2) . . ?
C12 C9B C6A 118.8(2) . . ?
C12 C9B C3A 110.2(2) . . ?
C6A C9B C3A 99.7(2) . . ?
C12 C9B C9A 114.5(2) . . ?
C6A C9B C9A 99.68(18) . . ?
C3A C9B C9A 112.8(2) . . ?
O7 C10 O8 123.1(3) . . ?
O7 C10 C6A 125.7(2) . . ?
O8 C10 C6A 111.3(2) . . ?
O8 C11 H11A 109.5 . . ?
O8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O9 C12 O10 122.8(2) . . ?
O9 C12 C9B 124.0(3) . . ?
O10 C12 C9B 113.1(2) . . ?
O10 C13 H13A 109.5 . . ?
O10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A C1 S2 O1 66.2(2) . . . . ?
C9A C1 S2 O2 -164.08(17) . . . . ?
C9A C1 S2 C3 -49.5(2) . . . . ?
O1 S2 C3 C3A -66.6(2) . . . . ?
O2 S2 C3 C3A 163.14(19) . . . . ?
C1 S2 C3 C3A 49.5(2) . . . . ?
C6 O4 C3A C3 177.9(2) . . . . ?
C6 O4 C3A C4 54.3(2) . . . . ?
C6 O4 C3A C9B -57.9(2) . . . . ?
S2 C3 C3A O4 61.9(3) . . . . ?
S2 C3 C3A C4 176.84(19) . . . . ?
S2 C3 C3A C9B -54.7(3) . . . . ?
C5 O3 C4 C3A -92.2(2) . . . . ?
O4 C3A C4 O3 27.9(3) . . . . ?
C3 C3A C4 O3 -93.3(3) . . . . ?
C9B C3A C4 O3 135.1(2) . . . . ?
O4 C3A C4 C5 -34.6(3) . . . . ?
C3 C3A C4 C5 -155.7(2) . . . . ?
C9B C3A C4 C5 72.7(3) . . . . ?
C4 O3 C5 C6 93.5(2) . . . . ?
C3A C4 C5 O3 109.0(2) . . . . ?
O3 C4 C5 C6 -107.5(2) . . . . ?
C3A C4 C5 C6 1.6(3) . . . . ?
C3A O4 C6 C5 -53.7(2) . . . . ?
C3A O4 C6 C6A 57.1(2) . . . . ?
O3 C5 C6 O4 -31.0(3) . . . . ?
C4 C5 C6 O4 31.7(3) . . . . ?
O3 C5 C6 C6A -137.9(2) . . . . ?
C4 C5 C6 C6A -75.2(3) . . . . ?
O4 C6 C6A C10 -158.72(19) . . . . ?
C5 C6 C6A C10 -52.1(3) . . . . ?
O4 C6 C6A C7 73.6(2) . . . . ?
C5 C6 C6A C7 -179.8(2) . . . . ?
O4 C6 C6A C9B -33.4(2) . . . . ?
C5 C6 C6A C9B 73.3(2) . . . . ?
C9A O5 C7 C8 53.6(2) . . . . ?
C9A O5 C7 C6A -58.1(2) . . . . ?
C10 C6A C7 O5 159.5(2) . . . . ?
C6 C6A C7 O5 -73.3(2) . . . . ?
C9B C6A C7 O5 33.7(2) . . . . ?
C10 C6A C7 C8 52.7(3) . . . . ?
C6 C6A C7 C8 179.9(2) . . . . ?
C9B C6A C7 C8 -73.1(3) . . . . ?
C9 O6 C8 C7 -94.1(2) . . . . ?
O5 C7 C8 C9 -31.5(2) . . . . ?
C6A C7 C8 C9 75.1(2) . . . . ?
O5 C7 C8 O6 30.8(2) . . . . ?
C6A C7 C8 O6 137.4(2) . . . . ?
C8 O6 C9 C9A 93.3(2) . . . . ?
C7 C8 C9 O6 106.1(2) . . . . ?
O6 C8 C9 C9A -107.9(2) . . . . ?
C7 C8 C9 C9A -1.8(2) . . . . ?
C7 O5 C9A C1 -178.0(2) . . . . ?
C7 O5 C9A C9 -54.2(2) . . . . ?
C7 O5 C9A C9B 59.0(2) . . . . ?
S2 C1 C9A O5 -61.2(2) . . . . ?
S2 C1 C9A C9 -175.79(17) . . . . ?
S2 C1 C9A C9B 53.7(3) . . . . ?
O6 C9 C9A O5 -28.8(3) . . . . ?
C8 C9 C9A O5 34.6(2) . . . . ?
O6 C9 C9A C1 91.9(3) . . . . ?
C8 C9 C9A C1 155.3(2) . . . . ?
O6 C9 C9A C9B -135.3(2) . . . . ?
C8 C9 C9A C9B -71.9(2) . . . . ?
C10 C6A C9B C12 2.3(3) . . . . ?
C6 C6A C9B C12 -120.4(2) . . . . ?
C7 C6A C9B C12 126.2(2) . . . . ?
C10 C6A C9B C3A 121.9(2) . . . . ?
C6 C6A C9B C3A -0.9(2) . . . . ?
C7 C6A C9B C3A -114.2(2) . . . . ?
C10 C6A C9B C9A -122.7(2) . . . . ?
C6 C6A C9B C9A 114.5(2) . . . . ?
C7 C6A C9B C9A 1.1(2) . . . . ?
O4 C3A C9B C12 161.0(2) . . . . ?
C3 C3A C9B C12 -77.0(3) . . . . ?
C4 C3A C9B C12 54.8(3) . . . . ?
O4 C3A C9B C6A 35.3(2) . . . . ?
C3 C3A C9B C6A 157.33(19) . . . . ?
C4 C3A C9B C6A -70.9(2) . . . . ?
O4 C3A C9B C9A -69.6(2) . . . . ?
C3 C3A C9B C9A 52.4(3) . . . . ?
C4 C3A C9B C9A -175.8(2) . . . . ?
O5 C9A C9B C12 -163.7(2) . . . . ?
C1 C9A C9B C12 75.6(3) . . . . ?
C9 C9A C9B C12 -57.8(3) . . . . ?
O5 C9A C9B C6A -35.8(3) . . . . ?
C1 C9A C9B C6A -156.5(2) . . . . ?
C9 C9A C9B C6A 70.1(2) . . . . ?
O5 C9A C9B C3A 69.1(3) . . . . ?
C1 C9A C9B C3A -51.6(3) . . . . ?
C9 C9A C9B C3A 175.0(2) . . . . ?
C11 O8 C10 O7 -0.7(4) . . . . ?
C11 O8 C10 C6A 179.1(2) . . . . ?
C6 C6A C10 O7 121.8(3) . . . . ?
C7 C6A C10 O7 -112.4(3) . . . . ?
C9B C6A C10 O7 5.1(4) . . . . ?
C6 C6A C10 O8 -58.0(3) . . . . ?
C7 C6A C10 O8 67.7(3) . . . . ?
C9B C6A C10 O8 -174.8(2) . . . . ?
C13 O10 C12 O9 -10.4(4) . . . . ?
C13 O10 C12 C9B 173.5(2) . . . . ?
C6A C9B C12 O9 99.2(3) . . . . ?
C3A C9B C12 O9 -14.8(4) . . . . ?
C9A C9B C12 O9 -143.3(3) . . . . ?
C6A C9B C12 O10 -84.8(3) . . . . ?
C3A C9B C12 O10 161.2(2) . . . . ?
C9A C9B C12 O10 32.7(3) . . . . ?

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.108

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_XB3
_database_code_depnum_ccdc_archive 'CCDC 2095409'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2021-07-09 deposited with the CCDC.	2021-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 N O9, 1.5(H2 O)'
_chemical_formula_sum            'C18 H22 N O10.50'
_chemical_formula_weight         420.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 '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 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 '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                   11.287(2)
_cell_length_b                   11.583(2)
_cell_length_c                   15.893(3)
_cell_angle_alpha                74.88(3)
_cell_angle_beta                 86.45(3)
_cell_angle_gamma                66.47(3)
_cell_volume                     1837.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      33.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             884
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.275
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_process_details   'Scala (Evans, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96990
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21043
_diffrn_reflns_av_unetI/netI     0.1566
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.315
_diffrn_reflns_theta_max         38.519
_diffrn_reflns_theta_full        35.587
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             7318
_reflns_number_gt                3945
_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       Automar
_computing_cell_refinement       iMosflm
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7318
_refine_ls_number_parameters     539
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1723
_refine_ls_wR_factor_gt          0.1420
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.951
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.96202(15) 0.89896(14) 0.31215(10) 0.0165(4) Uani 1 1 d . . . . .
O2 O 1.02362(15) 0.71665(14) 0.24429(10) 0.0132(4) Uani 1 1 d . . . . .
O3 O 0.98199(15) 0.58622(14) 0.14758(11) 0.0143(4) Uani 1 1 d . . . . .
O4 O 0.85671(16) 0.54751(15) 0.04593(11) 0.0205(5) Uani 1 1 d . . . . .
O5 O 1.33098(16) 0.68217(15) 0.13880(12) 0.0252(5) Uani 1 1 d . . . . .
O6 O 0.64604(16) 0.78257(16) 0.31031(12) 0.0217(5) Uani 1 1 d . . . . .
O7 O 0.59292(15) 0.81315(15) 0.17010(11) 0.0186(4) Uani 1 1 d . . . . .
O8 O 0.76806(16) 0.95886(15) -0.00787(11) 0.0232(5) Uani 1 1 d . . . . .
O9 O 0.68613(15) 1.01461(15) 0.11491(11) 0.0174(4) Uani 1 1 d . . . . .
C1 C 1.0437(2) 0.7215(2) 0.02377(16) 0.0154(6) Uani 1 1 d . . . . .
H1A H 1.0904 0.6437 0.0015 0.019 Uiso 1 1 calc R U . . .
H1B H 1.0074 0.7978 -0.0270 0.019 Uiso 1 1 calc R U . . .
N2 N 1.13479(19) 0.74132(18) 0.07501(13) 0.0157(5) Uani 1 1 d . . . . .
C3 C 1.0766(2) 0.8504(2) 0.11595(16) 0.0170(6) Uani 1 1 d . . . . .
H3A H 1.0397 0.9334 0.0701 0.020 Uiso 1 1 calc R U . . .
H3B H 1.1443 0.8548 0.1503 0.020 Uiso 1 1 calc R U . . .
C3A C 0.9715(2) 0.8333(2) 0.17492(16) 0.0134(6) Uani 1 1 d . . . . .
C4 C 0.9005(2) 0.9355(2) 0.22642(16) 0.0151(6) Uani 1 1 d . . . . .
H4 H 0.8457 1.0281 0.1966 0.018 Uiso 1 1 calc R U . . .
C5 C 0.8570(2) 0.8615(2) 0.30196(16) 0.0149(6) Uani 1 1 d . . . . .
H5 H 0.7709 0.9012 0.3266 0.018 Uiso 1 1 calc R U . . .
C6 C 0.9058(2) 0.7243(2) 0.28670(16) 0.0141(6) Uani 1 1 d . . . . .
H6 H 0.9165 0.6527 0.3407 0.017 Uiso 1 1 calc R U . . .
C6A C 0.8175(2) 0.7301(2) 0.21179(16) 0.0129(6) Uani 1 1 d . . . . .
C7 C 0.8617(2) 0.5965(2) 0.18708(16) 0.0141(6) Uani 1 1 d . . . . .
H7 H 0.8687 0.5211 0.2375 0.017 Uiso 1 1 calc R U . . .
C8 C 0.7783(2) 0.6122(2) 0.10873(16) 0.0165(6) Uani 1 1 d . . . . .
H8 H 0.6842 0.6298 0.1130 0.020 Uiso 1 1 calc R U . . .
C9 C 0.8281(2) 0.6834(2) 0.03459(17) 0.0166(6) Uani 1 1 d . . . . .
H9 H 0.7696 0.7525 -0.0145 0.020 Uiso 1 1 calc R U . . .
C9A C 0.9343(2) 0.7033(2) 0.07842(16) 0.0127(6) Uani 1 1 d . . . . .
C9B C 0.8654(2) 0.8095(2) 0.13027(15) 0.0126(6) Uani 1 1 d . . . . .
C10 C 1.2609(2) 0.6593(2) 0.09398(17) 0.0174(6) Uani 1 1 d . . . . .
C11 C 1.3161(2) 0.5424(2) 0.05657(18) 0.0247(7) Uani 1 1 d . . . . .
H11A H 1.4066 0.4911 0.0775 0.037 Uiso 1 1 calc R U . . .
H11B H 1.3115 0.5716 -0.0073 0.037 Uiso 1 1 calc R U . . .
H11C H 1.2662 0.4884 0.0752 0.037 Uiso 1 1 calc R U . . .
C12 C 0.6777(2) 0.7792(2) 0.23606(17) 0.0151(6) Uani 1 1 d . . . . .
C13 C 0.4573(2) 0.8596(3) 0.19146(18) 0.0259(7) Uani 1 1 d . . . . .
H13A H 0.4028 0.8880 0.1382 0.039 Uiso 1 1 calc R U . . .
H13B H 0.4365 0.9331 0.2174 0.039 Uiso 1 1 calc R U . . .
H13C H 0.4413 0.7890 0.2331 0.039 Uiso 1 1 calc R U . . .
C14 C 0.7676(2) 0.9341(2) 0.07119(17) 0.0149(6) Uani 1 1 d . . . . .
C15 C 0.5929(3) 1.1361(2) 0.06218(18) 0.0266(7) Uani 1 1 d . . . . .
H15A H 0.6380 1.1785 0.0185 0.040 Uiso 1 1 calc R U . . .
H15B H 0.5469 1.1936 0.0997 0.040 Uiso 1 1 calc R U . . .
H15C H 0.5307 1.1183 0.0327 0.040 Uiso 1 1 calc R U . . .
O10 O 0.14653(16) 0.44342(15) 0.46235(11) 0.0196(4) Uani 1 1 d . . . . .
O11 O 0.02379(15) 0.40997(14) 0.35608(11) 0.0140(4) Uani 1 1 d . . . . .
O12 O -0.01405(15) 0.28292(14) 0.25472(10) 0.0132(4) Uani 1 1 d . . . . .
O13 O 0.05063(15) 0.10373(15) 0.18350(10) 0.0172(4) Uani 1 1 d . . . . .
O14 O -0.31328(16) 0.33979(16) 0.33119(12) 0.0254(5) Uani 1 1 d . . . . .
O15 O 0.36304(16) 0.22420(16) 0.19399(12) 0.0227(5) Uani 1 1 d . . . . .
O16 O 0.41537(15) 0.18007(15) 0.33620(11) 0.0179(4) Uani 1 1 d . . . . .
O17 O 0.22724(16) 0.03262(15) 0.50933(11) 0.0212(5) Uani 1 1 d . . . . .
O18 O 0.31969(15) -0.01871(15) 0.38752(10) 0.0166(4) Uani 1 1 d . . . . .
C16 C -0.0717(2) 0.1480(2) 0.37967(16) 0.0162(6) Uani 1 1 d . . . . .
H16A H -0.1375 0.1430 0.3440 0.019 Uiso 1 1 calc R U . . .
H16B H -0.0365 0.0658 0.4263 0.019 Uiso 1 1 calc R U . . .
N17 N -0.13203(18) 0.25862(18) 0.41884(13) 0.0141(5) Uani 1 1 d . . . . .
C18 C -0.0435(2) 0.2742(2) 0.47515(16) 0.0148(6) Uani 1 1 d . . . . .
H18A H -0.0105 0.1965 0.5254 0.018 Uiso 1 1 calc R U . . .
H18B H -0.0909 0.3513 0.4981 0.018 Uiso 1 1 calc R U . . .
C18A C 0.0687(2) 0.2911(2) 0.42436(16) 0.0132(6) Uani 1 1 d . . . . .
C19 C 0.1746(2) 0.3085(2) 0.47118(16) 0.0159(6) Uani 1 1 d . . . . .
H19 H 0.2317 0.2380 0.5202 0.019 Uiso 1 1 calc R U . . .
C20 C 0.2265(2) 0.3807(2) 0.39932(16) 0.0162(6) Uani 1 1 d . . . . .
H20 H 0.3209 0.3625 0.3968 0.019 Uiso 1 1 calc R U . . .
C21 C 0.1454(2) 0.4003(2) 0.31870(16) 0.0144(6) Uani 1 1 d . . . . .
H21 H 0.1402 0.4766 0.2695 0.017 Uiso 1 1 calc R U . . .
C21A C 0.1913(2) 0.2673(2) 0.29235(16) 0.0131(6) Uani 1 1 d . . . . .
C22 C 0.1047(2) 0.2764(2) 0.21452(16) 0.0140(6) Uani 1 1 d . . . . .
H22 H 0.0955 0.3492 0.1616 0.017 Uiso 1 1 calc R U . . .
C23 C 0.1551(2) 0.1406(2) 0.19733(16) 0.0135(6) Uani 1 1 d . . . . .
H23 H 0.2422 0.1019 0.1736 0.016 Uiso 1 1 calc R U . . .
C24 C 0.1097(2) 0.0643(2) 0.27049(16) 0.0142(6) Uani 1 1 d . . . . .
H24 H 0.1640 -0.0288 0.2996 0.017 Uiso 1 1 calc R U . . .
C24A C 0.0359(2) 0.1644(2) 0.32314(16) 0.0129(6) Uani 1 1 d . . . . .
C24B C 0.1403(2) 0.1869(2) 0.37137(15) 0.0127(6) Uani 1 1 d . . . . .
C25 C -0.2511(2) 0.3505(2) 0.38886(16) 0.0159(6) Uani 1 1 d . . . . .
C26 C -0.3096(2) 0.4643(2) 0.42906(17) 0.0226(7) Uani 1 1 d . . . . .
H26A H -0.2592 0.5183 0.4145 0.034 Uiso 1 1 calc R U . . .
H26B H -0.3084 0.4320 0.4926 0.034 Uiso 1 1 calc R U . . .
H26C H -0.3990 0.5166 0.4062 0.034 Uiso 1 1 calc R U . . .
C27 C 0.3307(2) 0.2203(2) 0.26869(17) 0.0152(6) Uani 1 1 d . . . . .
C28 C 0.5504(2) 0.1374(3) 0.31377(18) 0.0250(7) Uani 1 1 d . . . . .
H28A H 0.5642 0.2100 0.2728 0.038 Uiso 1 1 calc R U . . .
H28B H 0.5725 0.0650 0.2866 0.038 Uiso 1 1 calc R U . . .
H28C H 0.6056 0.1085 0.3668 0.038 Uiso 1 1 calc R U . . .
C29 C 0.2346(2) 0.0600(2) 0.43042(17) 0.0145(6) Uani 1 1 d . . . . .
C30 C 0.4076(2) -0.1435(2) 0.44123(17) 0.0237(7) Uani 1 1 d . . . . .
H30A H 0.4620 -0.1968 0.4036 0.036 Uiso 1 1 calc R U . . .
H30B H 0.3575 -0.1888 0.4770 0.036 Uiso 1 1 calc R U . . .
H30C H 0.4625 -0.1290 0.4793 0.036 Uiso 1 1 calc R U . . .
O19 O 0.24420(17) 0.72405(17) 0.35305(12) 0.0303(5) Uani 1 1 d . . . . .
H19A H 0.1657 0.7433 0.3286 0.045 Uiso 1 1 d R U . . .
H19B H 0.3036 0.6509 0.3404 0.045 Uiso 1 1 d R U . . .
O20 O 0.76150(17) 0.27481(17) 0.16315(12) 0.0307(5) Uani 1 1 d . . . . .
H20A H 0.8481 0.2493 0.1680 0.046 Uiso 1 1 d R U . . .
H20B H 0.7224 0.3188 0.2032 0.046 Uiso 1 1 d R U . . .
O21 O 0.42469(17) 0.50183(17) 0.29528(12) 0.0379(6) Uani 1 1 d . . . . .
H21A H 0.4077 0.5516 0.2395 0.057 Uiso 1 1 d R U . . .
H21B H 0.5110 0.4541 0.3045 0.057 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.446(3) . ?
O1 C4 1.449(3) . ?
O2 C3A 1.434(3) . ?
O2 C6 1.434(3) . ?
O3 C9A 1.432(3) . ?
O3 C7 1.434(3) . ?
O4 C9 1.438(3) . ?
O4 C8 1.446(3) . ?
O5 C10 1.240(3) . ?
O6 C12 1.218(3) . ?
O7 C12 1.334(3) . ?
O7 C13 1.456(3) . ?
O8 C14 1.214(3) . ?
O9 C14 1.332(3) . ?
O9 C15 1.449(3) . ?
C1 N2 1.471(3) . ?
C1 C9A 1.517(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C10 1.357(3) . ?
N2 C3 1.471(3) . ?
C3 C3A 1.509(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4 1.542(3) . ?
C3A C9B 1.577(3) . ?
C4 C5 1.464(4) . ?
C4 H4 1.0000 . ?
C5 C6 1.540(3) . ?
C5 H5 1.0000 . ?
C6 C6A 1.570(3) . ?
C6 H6 1.0000 . ?
C6A C12 1.512(4) . ?
C6A C7 1.573(3) . ?
C6A C9B 1.583(4) . ?
C7 C8 1.536(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.472(4) . ?
C8 H8 1.0000 . ?
C9 C9A 1.544(3) . ?
C9 H9 1.0000 . ?
C9A C9B 1.576(3) . ?
C9B C14 1.527(3) . ?
C10 C11 1.509(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O10 C19 1.435(3) . ?
O10 C20 1.446(3) . ?
O11 C21 1.435(3) . ?
O11 C18A 1.436(3) . ?
O12 C22 1.431(3) . ?
O12 C24A 1.437(3) . ?
O13 C24 1.451(3) . ?
O13 C23 1.451(3) . ?
O14 C25 1.247(3) . ?
O15 C27 1.215(3) . ?
O16 C27 1.339(3) . ?
O16 C28 1.456(3) . ?
O17 C29 1.217(3) . ?
O18 C29 1.328(3) . ?
O18 C30 1.456(3) . ?
C16 N17 1.470(3) . ?
C16 C24A 1.509(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
N17 C25 1.356(3) . ?
N17 C18 1.474(3) . ?
C18 C18A 1.511(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18A C19 1.550(3) . ?
C18A C24B 1.577(3) . ?
C19 C20 1.469(4) . ?
C19 H19 1.0000 . ?
C20 C21 1.536(3) . ?
C20 H20 1.0000 . ?
C21 C21A 1.578(3) . ?
C21 H21 1.0000 . ?
C21A C27 1.504(4) . ?
C21A C22 1.580(3) . ?
C21A C24B 1.582(4) . ?
C22 C23 1.537(3) . ?
C22 H22 1.0000 . ?
C23 C24 1.466(4) . ?
C23 H23 1.0000 . ?
C24 C24A 1.545(3) . ?
C24 H24 1.0000 . ?
C24A C24B 1.584(3) . ?
C24B C29 1.525(3) . ?
C25 C26 1.508(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
O19 H19A 0.9087 . ?
O19 H19B 0.9090 . ?
O20 H20A 0.9029 . ?
O20 H20B 0.9031 . ?
O21 H21A 0.9061 . ?
O21 H21B 0.9061 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C4 60.74(15) . . ?
C3A O2 C6 98.42(17) . . ?
C9A O3 C7 98.37(17) . . ?
C9 O4 C8 61.35(15) . . ?
C12 O7 C13 115.69(19) . . ?
C14 O9 C15 115.9(2) . . ?
N2 C1 C9A 111.29(19) . . ?
N2 C1 H1A 109.4 . . ?
C9A C1 H1A 109.4 . . ?
N2 C1 H1B 109.4 . . ?
C9A C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C10 N2 C1 124.79(18) . . ?
C10 N2 C3 119.64(18) . . ?
C1 N2 C3 115.13(18) . . ?
N2 C3 C3A 110.60(19) . . ?
N2 C3 H3A 109.5 . . ?
C3A C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
C3A C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
O2 C3A C3 110.63(19) . . ?
O2 C3A C4 101.24(18) . . ?
C3 C3A C4 119.0(2) . . ?
O2 C3A C9B 101.96(18) . . ?
C3 C3A C9B 114.52(19) . . ?
C4 C3A C9B 107.40(18) . . ?
O1 C4 C5 59.53(15) . . ?
O1 C4 C3A 111.49(17) . . ?
C5 C4 C3A 102.99(19) . . ?
O1 C4 H4 121.9 . . ?
C5 C4 H4 121.9 . . ?
C3A C4 H4 121.9 . . ?
O1 C5 C4 59.73(15) . . ?
O1 C5 C6 112.15(18) . . ?
C4 C5 C6 103.6(2) . . ?
O1 C5 H5 121.6 . . ?
C4 C5 H5 121.6 . . ?
C6 C5 H5 121.6 . . ?
O2 C6 C5 100.85(19) . . ?
O2 C6 C6A 102.78(18) . . ?
C5 C6 C6A 107.91(18) . . ?
O2 C6 H6 114.6 . . ?
C5 C6 H6 114.6 . . ?
C6A C6 H6 114.6 . . ?
C12 C6A C6 109.84(19) . . ?
C12 C6A C7 112.07(19) . . ?
C6 C6A C7 112.80(18) . . ?
C12 C6A C9B 121.40(19) . . ?
C6 C6A C9B 100.34(18) . . ?
C7 C6A C9B 99.71(18) . . ?
O3 C7 C8 101.35(19) . . ?
O3 C7 C6A 101.74(18) . . ?
C8 C7 C6A 109.98(18) . . ?
O3 C7 H7 114.1 . . ?
C8 C7 H7 114.1 . . ?
C6A C7 H7 114.1 . . ?
O4 C8 C9 59.07(15) . . ?
O4 C8 C7 111.28(19) . . ?
C9 C8 C7 103.3(2) . . ?
O4 C8 H8 122.0 . . ?
C9 C8 H8 122.0 . . ?
C7 C8 H8 122.0 . . ?
O4 C9 C8 59.58(16) . . ?
O4 C9 C9A 111.71(18) . . ?
C8 C9 C9A 102.85(19) . . ?
O4 C9 H9 121.9 . . ?
C8 C9 H9 121.9 . . ?
C9A C9 H9 121.9 . . ?
O3 C9A C1 110.95(18) . . ?
O3 C9A C9 101.04(19) . . ?
C1 C9A C9 118.37(19) . . ?
O3 C9A C9B 101.76(18) . . ?
C1 C9A C9B 114.85(19) . . ?
C9 C9A C9B 107.77(18) . . ?
C14 C9B C9A 111.12(19) . . ?
C14 C9B C3A 113.00(19) . . ?
C9A C9B C3A 109.01(18) . . ?
C14 C9B C6A 119.7(2) . . ?
C9A C9B C6A 101.69(18) . . ?
C3A C9B C6A 101.22(17) . . ?
O5 C10 N2 120.8(2) . . ?
O5 C10 C11 120.3(2) . . ?
N2 C10 C11 118.8(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O6 C12 O7 123.1(2) . . ?
O6 C12 C6A 122.6(2) . . ?
O7 C12 C6A 114.3(2) . . ?
O7 C13 H13A 109.5 . . ?
O7 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O7 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O8 C14 O9 123.6(2) . . ?
O8 C14 C9B 122.9(2) . . ?
O9 C14 C9B 113.4(2) . . ?
O9 C15 H15A 109.5 . . ?
O9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C19 O10 C20 61.32(15) . . ?
C21 O11 C18A 98.82(17) . . ?
C22 O12 C24A 98.72(17) . . ?
C24 O13 C23 60.67(15) . . ?
C27 O16 C28 114.82(19) . . ?
C29 O18 C30 115.7(2) . . ?
N17 C16 C24A 109.99(19) . . ?
N17 C16 H16A 109.7 . . ?
C24A C16 H16A 109.7 . . ?
N17 C16 H16B 109.7 . . ?
C24A C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C25 N17 C16 119.68(18) . . ?
C25 N17 C18 124.38(18) . . ?
C16 N17 C18 114.54(17) . . ?
N17 C18 C18A 110.41(19) . . ?
N17 C18 H18A 109.6 . . ?
C18A C18 H18A 109.6 . . ?
N17 C18 H18B 109.6 . . ?
C18A C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
O11 C18A C18 110.35(18) . . ?
O11 C18A C19 100.74(18) . . ?
C18 C18A C19 119.2(2) . . ?
O11 C18A C24B 101.66(18) . . ?
C18 C18A C24B 115.45(19) . . ?
C19 C18A C24B 107.10(18) . . ?
O10 C19 C20 59.71(15) . . ?
O10 C19 C18A 111.72(18) . . ?
C20 C19 C18A 102.94(19) . . ?
O10 C19 H19 121.9 . . ?
C20 C19 H19 121.9 . . ?
C18A C19 H19 121.9 . . ?
O10 C20 C19 58.96(15) . . ?
O10 C20 C21 111.33(19) . . ?
C19 C20 C21 103.7(2) . . ?
O10 C20 H20 121.9 . . ?
C19 C20 H20 121.9 . . ?
C21 C20 H20 121.9 . . ?
O11 C21 C20 101.22(19) . . ?
O11 C21 C21A 101.77(18) . . ?
C20 C21 C21A 109.16(18) . . ?
O11 C21 H21 114.4 . . ?
C20 C21 H21 114.4 . . ?
C21A C21 H21 114.4 . . ?
C27 C21A C21 112.02(19) . . ?
C27 C21A C22 109.24(19) . . ?
C21 C21A C22 112.24(18) . . ?
C27 C21A C24B 122.57(19) . . ?
C21 C21A C24B 99.77(18) . . ?
C22 C21A C24B 100.31(18) . . ?
O12 C22 C23 101.00(19) . . ?
O12 C22 C21A 102.75(18) . . ?
C23 C22 C21A 107.42(18) . . ?
O12 C22 H22 114.7 . . ?
C23 C22 H22 114.7 . . ?
C21A C22 H22 114.7 . . ?
O13 C23 C24 59.66(15) . . ?
O13 C23 C22 112.05(18) . . ?
C24 C23 C22 103.8(2) . . ?
O13 C23 H23 121.6 . . ?
C24 C23 H23 121.6 . . ?
C22 C23 H23 121.6 . . ?
O13 C24 C23 59.67(15) . . ?
O13 C24 C24A 111.30(17) . . ?
C23 C24 C24A 102.86(19) . . ?
O13 C24 H24 122.0 . . ?
C23 C24 H24 122.0 . . ?
C24A C24 H24 122.0 . . ?
O12 C24A C16 110.23(19) . . ?
O12 C24A C24 101.21(18) . . ?
C16 C24A C24 120.0(2) . . ?
O12 C24A C24B 101.60(18) . . ?
C16 C24A C24B 114.13(19) . . ?
C24 C24A C24B 107.39(18) . . ?
C29 C24B C18A 111.33(19) . . ?
C29 C24B C21A 120.3(2) . . ?
C18A C24B C21A 102.02(18) . . ?
C29 C24B C24A 111.82(19) . . ?
C18A C24B C24A 109.03(18) . . ?
C21A C24B C24A 101.35(17) . . ?
O14 C25 N17 121.2(2) . . ?
O14 C25 C26 120.3(2) . . ?
N17 C25 C26 118.5(2) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O15 C27 O16 123.0(2) . . ?
O15 C27 C21A 122.6(2) . . ?
O16 C27 C21A 114.3(2) . . ?
O16 C28 H28A 109.5 . . ?
O16 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O16 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O17 C29 O18 123.9(2) . . ?
O17 C29 C24B 122.2(2) . . ?
O18 C29 C24B 113.9(2) . . ?
O18 C30 H30A 109.5 . . ?
O18 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O18 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
H19A O19 H19B 109.5 . . ?
H20A O20 H20B 110.5 . . ?
H21A O21 H21B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A C1 N2 C10 116.3(3) . . . . ?
C9A C1 N2 C3 -56.1(3) . . . . ?
C10 N2 C3 C3A -115.3(2) . . . . ?
C1 N2 C3 C3A 57.5(3) . . . . ?
C6 O2 C3A C3 -178.76(16) . . . . ?
C6 O2 C3A C4 54.17(19) . . . . ?
C6 O2 C3A C9B -56.54(18) . . . . ?
N2 C3 C3A O2 61.8(2) . . . . ?
N2 C3 C3A C4 178.29(18) . . . . ?
N2 C3 C3A C9B -52.8(3) . . . . ?
C5 O1 C4 C3A -92.8(2) . . . . ?
O2 C3A C4 O1 29.5(2) . . . . ?
C3 C3A C4 O1 -91.9(3) . . . . ?
C9B C3A C4 O1 135.9(2) . . . . ?
O2 C3A C4 C5 -32.6(2) . . . . ?
C3 C3A C4 C5 -154.0(2) . . . . ?
C9B C3A C4 C5 73.9(2) . . . . ?
C4 O1 C5 C6 93.2(2) . . . . ?
C3A C4 C5 O1 107.48(18) . . . . ?
O1 C4 C5 C6 -107.96(18) . . . . ?
C3A C4 C5 C6 -0.5(2) . . . . ?
C3A O2 C6 C5 -54.30(18) . . . . ?
C3A O2 C6 C6A 57.08(18) . . . . ?
O1 C5 C6 O2 -29.1(2) . . . . ?
C4 C5 C6 O2 33.4(2) . . . . ?
O1 C5 C6 C6A -136.5(2) . . . . ?
C4 C5 C6 C6A -74.0(2) . . . . ?
O2 C6 C6A C12 -162.82(18) . . . . ?
C5 C6 C6A C12 -56.8(3) . . . . ?
O2 C6 C6A C7 71.4(2) . . . . ?
C5 C6 C6A C7 177.4(2) . . . . ?
O2 C6 C6A C9B -33.84(19) . . . . ?
C5 C6 C6A C9B 72.2(2) . . . . ?
C9A O3 C7 C8 54.19(18) . . . . ?
C9A O3 C7 C6A -59.25(18) . . . . ?
C12 C6A C7 O3 166.84(18) . . . . ?
C6 C6A C7 O3 -68.6(2) . . . . ?
C9B C6A C7 O3 37.07(19) . . . . ?
C12 C6A C7 C8 60.0(3) . . . . ?
C6 C6A C7 C8 -175.4(2) . . . . ?
C9B C6A C7 C8 -69.8(2) . . . . ?
C9 O4 C8 C7 -93.1(2) . . . . ?
O3 C7 C8 O4 29.3(2) . . . . ?
C6A C7 C8 O4 136.4(2) . . . . ?
O3 C7 C8 C9 -32.4(2) . . . . ?
C6A C7 C8 C9 74.7(2) . . . . ?
C8 O4 C9 C9A 92.5(2) . . . . ?
C7 C8 C9 O4 107.04(18) . . . . ?
O4 C8 C9 C9A -107.82(18) . . . . ?
C7 C8 C9 C9A -0.8(2) . . . . ?
C7 O3 C9A C1 179.03(16) . . . . ?
C7 O3 C9A C9 -54.59(18) . . . . ?
C7 O3 C9A C9B 56.40(18) . . . . ?
N2 C1 C9A O3 -64.9(2) . . . . ?
N2 C1 C9A C9 179.03(18) . . . . ?
N2 C1 C9A C9B 49.8(3) . . . . ?
O4 C9 C9A O3 -28.3(2) . . . . ?
C8 C9 C9A O3 33.7(2) . . . . ?
O4 C9 C9A C1 92.9(3) . . . . ?
C8 C9 C9A C1 155.03(19) . . . . ?
O4 C9 C9A C9B -134.6(2) . . . . ?
C8 C9 C9A C9B -72.5(2) . . . . ?
O3 C9A C9B C14 -159.92(19) . . . . ?
C1 C9A C9B C14 80.2(2) . . . . ?
C9 C9A C9B C14 -54.1(3) . . . . ?
O3 C9A C9B C3A 74.9(2) . . . . ?
C1 C9A C9B C3A -45.0(3) . . . . ?
C9 C9A C9B C3A -179.3(2) . . . . ?
O3 C9A C9B C6A -31.4(2) . . . . ?
C1 C9A C9B C6A -151.36(18) . . . . ?
C9 C9A C9B C6A 74.4(2) . . . . ?
O2 C3A C9B C14 163.06(19) . . . . ?
C3 C3A C9B C14 -77.4(3) . . . . ?
C4 C3A C9B C14 57.1(3) . . . . ?
O2 C3A C9B C9A -72.9(2) . . . . ?
C3 C3A C9B C9A 46.6(3) . . . . ?
C4 C3A C9B C9A -178.85(19) . . . . ?
O2 C3A C9B C6A 33.8(2) . . . . ?
C3 C3A C9B C6A 153.30(18) . . . . ?
C4 C3A C9B C6A -72.2(2) . . . . ?
C12 C6A C9B C14 -3.9(3) . . . . ?
C6 C6A C9B C14 -124.9(2) . . . . ?
C7 C6A C9B C14 119.6(2) . . . . ?
C12 C6A C9B C9A -126.7(2) . . . . ?
C6 C6A C9B C9A 112.31(17) . . . . ?
C7 C6A C9B C9A -3.22(19) . . . . ?
C12 C6A C9B C3A 121.0(2) . . . . ?
C6 C6A C9B C3A -0.04(19) . . . . ?
C7 C6A C9B C3A -115.56(17) . . . . ?
C1 N2 C10 O5 -178.9(2) . . . . ?
C3 N2 C10 O5 -6.9(4) . . . . ?
C1 N2 C10 C11 3.5(4) . . . . ?
C3 N2 C10 C11 175.6(2) . . . . ?
C13 O7 C12 O6 2.0(3) . . . . ?
C13 O7 C12 C6A 179.39(19) . . . . ?
C6 C6A C12 O6 -15.8(3) . . . . ?
C7 C6A C12 O6 110.4(3) . . . . ?
C9B C6A C12 O6 -132.2(2) . . . . ?
C6 C6A C12 O7 166.81(18) . . . . ?
C7 C6A C12 O7 -67.0(3) . . . . ?
C9B C6A C12 O7 50.5(3) . . . . ?
C15 O9 C14 O8 1.4(4) . . . . ?
C15 O9 C14 C9B 178.6(2) . . . . ?
C9A C9B C14 O8 -17.5(3) . . . . ?
C3A C9B C14 O8 105.4(3) . . . . ?
C6A C9B C14 O8 -135.6(2) . . . . ?
C9A C9B C14 O9 165.3(2) . . . . ?
C3A C9B C14 O9 -71.8(3) . . . . ?
C6A C9B C14 O9 47.2(3) . . . . ?
C24A C16 N17 C25 106.5(2) . . . . ?
C24A C16 N17 C18 -60.5(3) . . . . ?
C25 N17 C18 C18A -108.1(3) . . . . ?
C16 N17 C18 C18A 58.3(3) . . . . ?
C21 O11 C18A C18 -178.91(16) . . . . ?
C21 O11 C18A C19 54.25(18) . . . . ?
C21 O11 C18A C24B -55.92(18) . . . . ?
N17 C18 C18A O11 64.6(2) . . . . ?
N17 C18 C18A C19 -179.68(18) . . . . ?
N17 C18 C18A C24B -50.0(3) . . . . ?
C20 O10 C19 C18A -92.7(2) . . . . ?
O11 C18A C19 O10 28.7(2) . . . . ?
C18 C18A C19 O10 -92.0(3) . . . . ?
C24B C18A C19 O10 134.6(2) . . . . ?
O11 C18A C19 C20 -33.5(2) . . . . ?
C18 C18A C19 C20 -154.3(2) . . . . ?
C24B C18A C19 C20 72.4(2) . . . . ?
C19 O10 C20 C21 93.5(2) . . . . ?
C18A C19 C20 O10 107.79(18) . . . . ?
O10 C19 C20 C21 -106.88(18) . . . . ?
C18A C19 C20 C21 0.9(2) . . . . ?
C18A O11 C21 C20 -53.84(18) . . . . ?
C18A O11 C21 C21A 58.69(18) . . . . ?
O10 C20 C21 O11 -29.7(2) . . . . ?
C19 C20 C21 O11 32.0(2) . . . . ?
O10 C20 C21 C21A -136.5(2) . . . . ?
C19 C20 C21 C21A -74.8(2) . . . . ?
O11 C21 C21A C27 -167.82(19) . . . . ?
C20 C21 C21A C27 -61.4(3) . . . . ?
O11 C21 C21A C22 68.9(2) . . . . ?
C20 C21 C21A C22 175.3(2) . . . . ?
O11 C21 C21A C24B -36.61(19) . . . . ?
C20 C21 C21A C24B 69.8(2) . . . . ?
C24A O12 C22 C23 53.92(18) . . . . ?
C24A O12 C22 C21A -56.97(18) . . . . ?
C27 C21A C22 O12 163.34(18) . . . . ?
C21 C21A C22 O12 -71.8(2) . . . . ?
C24B C21A C22 O12 33.32(19) . . . . ?
C27 C21A C22 C23 57.3(3) . . . . ?
C21 C21A C22 C23 -177.8(2) . . . . ?
C24B C21A C22 C23 -72.7(2) . . . . ?
C24 O13 C23 C22 -93.5(2) . . . . ?
O12 C22 C23 O13 29.4(2) . . . . ?
C21A C22 C23 O13 136.7(2) . . . . ?
O12 C22 C23 C24 -33.1(2) . . . . ?
C21A C22 C23 C24 74.2(2) . . . . ?
C23 O13 C24 C24A 92.8(2) . . . . ?
C22 C23 C24 O13 107.71(18) . . . . ?
O13 C23 C24 C24A -107.34(17) . . . . ?
C22 C23 C24 C24A 0.4(2) . . . . ?
C22 O12 C24A C16 178.14(16) . . . . ?
C22 O12 C24A C24 -53.81(19) . . . . ?
C22 O12 C24A C24B 56.78(18) . . . . ?
N17 C16 C24A O12 -59.7(2) . . . . ?
N17 C16 C24A C24 -176.62(18) . . . . ?
N17 C16 C24A C24B 53.8(2) . . . . ?
O13 C24 C24A O12 -29.8(2) . . . . ?
C23 C24 C24A O12 32.4(2) . . . . ?
O13 C24 C24A C16 91.6(3) . . . . ?
C23 C24 C24A C16 153.8(2) . . . . ?
O13 C24 C24A C24B -135.9(2) . . . . ?
C23 C24 C24A C24B -73.7(2) . . . . ?
O11 C18A C24B C29 160.68(19) . . . . ?
C18 C18A C24B C29 -79.9(2) . . . . ?
C19 C18A C24B C29 55.5(3) . . . . ?
O11 C18A C24B C21A 31.1(2) . . . . ?
C18 C18A C24B C21A 150.59(19) . . . . ?
C19 C18A C24B C21A -74.1(2) . . . . ?
O11 C18A C24B C24A -75.5(2) . . . . ?
C18 C18A C24B C24A 44.0(3) . . . . ?
C19 C18A C24B C24A 179.30(19) . . . . ?
C27 C21A C24B C29 3.5(3) . . . . ?
C21 C21A C24B C29 -120.6(2) . . . . ?
C22 C21A C24B C29 124.4(2) . . . . ?
C27 C21A C24B C18A 127.2(2) . . . . ?
C21 C21A C24B C18A 3.08(19) . . . . ?
C22 C21A C24B C18A -111.86(17) . . . . ?
C27 C21A C24B C24A -120.3(2) . . . . ?
C21 C21A C24B C24A 115.58(17) . . . . ?
C22 C21A C24B C24A 0.64(19) . . . . ?
O12 C24A C24B C29 -163.52(19) . . . . ?
C16 C24A C24B C29 77.9(2) . . . . ?
C24 C24A C24B C29 -57.7(3) . . . . ?
O12 C24A C24B C18A 72.9(2) . . . . ?
C16 C24A C24B C18A -45.7(3) . . . . ?
C24 C24A C24B C18A 178.74(19) . . . . ?
O12 C24A C24B C21A -34.2(2) . . . . ?
C16 C24A C24B C21A -152.76(18) . . . . ?
C24 C24A C24B C21A 71.6(2) . . . . ?
C16 N17 C25 O14 3.4(4) . . . . ?
C18 N17 C25 O14 169.1(2) . . . . ?
C16 N17 C25 C26 -178.8(2) . . . . ?
C18 N17 C25 C26 -13.1(4) . . . . ?
C28 O16 C27 O15 -1.8(3) . . . . ?
C28 O16 C27 C21A -178.52(19) . . . . ?
C21 C21A C27 O15 -107.0(3) . . . . ?
C22 C21A C27 O15 18.0(3) . . . . ?
C24B C21A C27 O15 134.6(2) . . . . ?
C21 C21A C27 O16 69.7(3) . . . . ?
C22 C21A C27 O16 -165.26(18) . . . . ?
C24B C21A C27 O16 -48.6(3) . . . . ?
C30 O18 C29 O17 -0.4(3) . . . . ?
C30 O18 C29 C24B -177.3(2) . . . . ?
C18A C24B C29 O17 18.8(3) . . . . ?
C21A C24B C29 O17 138.0(2) . . . . ?
C24A C24B C29 O17 -103.4(3) . . . . ?
C18A C24B C29 O18 -164.3(2) . . . . ?
C21A C24B C29 O18 -45.1(3) . . . . ?
C24A C24B C29 O18 73.5(3) . . . . ?

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
C1 H1A O4 0.99 2.36 3.324(3) 163.3 2_765
C1 H1B O13 0.99 2.46 3.364(3) 152.0 2_665
C4 H4 O20 1.00 2.54 3.483(3) 157.1 1_565
C6 H6 O11 1.00 2.53 3.234(3) 127.4 1_655
C7 H7 O11 1.00 2.37 3.107(3) 129.9 1_655
C7 H7 O12 1.00 2.48 3.225(3) 130.5 1_655
C15 H15B O15 0.98 2.45 3.239(3) 137.6 1_565
C18 H18A O1 0.99 2.53 3.416(3) 149.1 2_666
C18 H18B O10 0.99 2.45 3.399(3) 161.3 2_566
C21 H21 O2 1.00 2.49 3.261(3) 133.9 1_455
C21 H21 O3 1.00 2.43 3.135(3) 127.3 1_455
C22 H22 O3 1.00 2.48 3.186(3) 127.5 1_455
C24 H24 O19 1.00 2.55 3.511(3) 161.7 1_545
C26 H26B O19 0.98 2.58 3.519(4) 159.9 2_566
C28 H28C O17 0.98 2.54 3.481(3) 162.2 2_656
C30 H30A O6 0.98 2.44 3.271(3) 141.8 1_545
O19 H19A O1 0.91 2.26 3.015(3) 139.7 1_455
O19 H19A O2 0.91 2.31 3.158(2) 155.2 1_455
O19 H19B O21 0.91 2.00 2.904(3) 172.1 .
O20 H20A O12 0.90 2.35 3.044(2) 134.0 1_655
O20 H20A O13 0.90 2.21 3.052(3) 154.0 1_655
O20 H20B O14 0.90 2.11 2.945(3) 154.1 1_655
O21 H21A O5 0.91 1.86 2.742(3) 163.6 1_455
O21 H21B O14 0.91 1.89 2.795(3) 173.9 1_655

_refine_diff_density_max         0.549
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.082

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_EP89
_database_code_depnum_ccdc_archive 'CCDC 2095410'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2021-07-09 deposited with the CCDC.	2021-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 N O9, C H Cl3'
_chemical_formula_sum            'C24 H22 Cl3 N O9'
_chemical_formula_weight         574.78

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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   11.7306(2)
_cell_length_b                   14.9240(3)
_cell_length_c                   27.2575(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4771.90(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      31.67

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_F_000             2368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.442
_shelx_estimated_absorpt_T_min   0.898
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            106676
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.1052
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.291
_diffrn_reflns_theta_max         32.585
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8698
_reflns_number_gt                6308
_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, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'

_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)+(0.0338P)²+2.8999P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00046(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8698
_refine_ls_number_parameters     337
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1014
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
O1 O 0.11749(9) 0.58722(7) 0.54650(4) 0.0163(2) Uani 1 1 d . . . . .
O2 O 0.28391(9) 0.51301(7) 0.50966(4) 0.0115(2) Uani 1 1 d . . . . .
O3 O 0.45624(9) 0.40286(7) 0.51026(4) 0.0114(2) Uani 1 1 d . . . . .
O4 O 0.57998(9) 0.28958(8) 0.54739(4) 0.0174(2) Uani 1 1 d . . . . .
O5 O 0.31037(10) 0.28949(8) 0.38669(4) 0.0192(2) Uani 1 1 d . . . . .
O6 O 0.31453(10) 0.49417(8) 0.66398(4) 0.0202(2) Uani 1 1 d . . . . .
O7 O 0.50179(10) 0.50085(8) 0.64679(4) 0.0181(2) Uani 1 1 d . . . . .
O8 O 0.29931(10) 0.30647(8) 0.63821(4) 0.0195(2) Uani 1 1 d . . . . .
O9 O 0.14079(9) 0.30788(8) 0.59218(4) 0.0157(2) Uani 1 1 d . . . . .
C1 C 0.32476(13) 0.28526(10) 0.48760(5) 0.0124(3) Uani 1 1 d . . . . .
H1A H 0.3831 0.2591 0.4656 0.015 Uiso 1 1 calc R U . . .
H1B H 0.2781 0.2358 0.5011 0.015 Uiso 1 1 calc R U . . .
N2 N 0.25192(10) 0.34666(8) 0.45975(4) 0.0115(2) Uani 1 1 d . . . . .
C3 C 0.16140(12) 0.38921(10) 0.48851(5) 0.0121(3) Uani 1 1 d . . . . .
H3A H 0.1105 0.3427 0.5024 0.015 Uiso 1 1 calc R U . . .
H3B H 0.1153 0.4287 0.4671 0.015 Uiso 1 1 calc R U . . .
C3A C 0.21324(12) 0.44338(10) 0.52940(5) 0.0107(3) Uani 1 1 d . . . . .
C4 C 0.13466(13) 0.49683(10) 0.56345(5) 0.0132(3) Uani 1 1 d . . . . .
H4 H 0.0787 0.4665 0.5856 0.016 Uiso 1 1 calc R U . . .
C5 C 0.20842(13) 0.56920(10) 0.58088(6) 0.0137(3) Uani 1 1 d . . . . .
H5 H 0.2055 0.5910 0.6155 0.016 Uiso 1 1 calc R U . . .
C6 C 0.32223(12) 0.55077(10) 0.55469(5) 0.0121(3) Uani 1 1 d . . . . .
H6 H 0.3724 0.6045 0.5509 0.015 Uiso 1 1 calc R U . . .
C6A C 0.38079(12) 0.46842(10) 0.58065(5) 0.0104(3) Uani 1 1 d . . . . .
C7 C 0.49494(12) 0.43946(10) 0.55596(5) 0.0119(3) Uani 1 1 d . . . . .
H7 H 0.5528 0.4883 0.5528 0.014 Uiso 1 1 calc R U . . .
C8 C 0.53800(13) 0.35480(10) 0.58185(6) 0.0135(3) Uani 1 1 d . . . . .
H8 H 0.5643 0.3559 0.6167 0.016 Uiso 1 1 calc R U . . .
C9 C 0.46353(13) 0.28412(10) 0.56330(6) 0.0127(3) Uani 1 1 d . . . . .
H9 H 0.4361 0.2344 0.5848 0.015 Uiso 1 1 calc R U . . .
C9A C 0.38253(12) 0.33508(10) 0.52907(5) 0.0110(3) Uani 1 1 d . . . . .
C9B C 0.29915(12) 0.39101(10) 0.56289(5) 0.0104(3) Uani 1 1 d . . . . .
C10 C 0.25081(13) 0.34273(10) 0.41026(5) 0.0133(3) Uani 1 1 d . . . . .
C11 C 0.17617(13) 0.40838(10) 0.38342(5) 0.0131(3) Uani 1 1 d . . . . .
C12 C 0.19313(13) 0.50043(11) 0.38816(6) 0.0162(3) Uani 1 1 d . . . . .
H12 H 0.2499 0.5225 0.4099 0.019 Uiso 1 1 calc R U . . .
C13 C 0.12703(15) 0.55989(11) 0.36113(6) 0.0190(3) Uani 1 1 d . . . . .
H13 H 0.1399 0.6226 0.3637 0.023 Uiso 1 1 calc R U . . .
C14 C 0.04215(15) 0.52753(12) 0.33042(6) 0.0190(3) Uani 1 1 d . . . . .
H14 H -0.0038 0.5682 0.3123 0.023 Uiso 1 1 calc R U . . .
C15 C 0.02407(14) 0.43585(11) 0.32604(6) 0.0178(3) Uani 1 1 d . . . . .
H15 H -0.0349 0.4140 0.3053 0.021 Uiso 1 1 calc R U . . .
C16 C 0.09220(13) 0.37594(11) 0.35193(6) 0.0155(3) Uani 1 1 d . . . . .
H16 H 0.0815 0.3132 0.3482 0.019 Uiso 1 1 calc R U . . .
C17 C 0.39197(13) 0.48675(10) 0.63524(6) 0.0135(3) Uani 1 1 d . . . . .
C18 C 0.52384(17) 0.52350(13) 0.69763(6) 0.0259(4) Uani 1 1 d . . . . .
H18A H 0.6063 0.5258 0.7032 0.039 Uiso 1 1 calc R U . . .
H18B H 0.4899 0.4779 0.7190 0.039 Uiso 1 1 calc R U . . .
H18C H 0.4902 0.5821 0.7050 0.039 Uiso 1 1 calc R U . . .
C19 C 0.24828(13) 0.33218(10) 0.60269(5) 0.0124(3) Uani 1 1 d . . . . .
C20 C 0.08750(14) 0.25080(11) 0.62889(6) 0.0182(3) Uani 1 1 d . . . . .
H20A H 0.0090 0.2375 0.6190 0.027 Uiso 1 1 calc R U . . .
H20B H 0.0871 0.2817 0.6606 0.027 Uiso 1 1 calc R U . . .
H20C H 0.1305 0.1948 0.6318 0.027 Uiso 1 1 calc R U . . .
Cl1 Cl 0.25986(3) 0.64701(3) 0.73629(2) 0.01942(9) Uani 1 1 d . . . . .
Cl2 Cl 0.06823(3) 0.76592(3) 0.75151(2) 0.02094(9) Uani 1 1 d . . . . .
Cl3 Cl 0.29802(4) 0.83216(3) 0.76539(2) 0.02809(11) Uani 1 1 d . . . . .
C21 C 0.20752(13) 0.73815(12) 0.77083(6) 0.0181(3) Uani 1 1 d . . . . .
H21 H 0.2045 0.7200 0.8061 0.022 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.4400(18) . ?
O1 C5 1.4450(18) . ?
O2 C6 1.4236(18) . ?
O2 C3A 1.4342(17) . ?
O3 C9A 1.4261(17) . ?
O3 C7 1.4339(17) . ?
O4 C9 1.4356(19) . ?
O4 C8 1.4395(18) . ?
O5 C10 1.2379(18) . ?
O6 C17 1.2047(19) . ?
O7 C17 1.3427(19) . ?
O7 C18 1.450(2) . ?
O8 C19 1.2012(18) . ?
O9 C19 1.3430(18) . ?
O9 C20 1.4553(18) . ?
C1 N2 1.4650(19) . ?
C1 C9A 1.513(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C10 1.3501(18) . ?
N2 C3 1.4648(18) . ?
C3 C3A 1.505(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4 1.532(2) . ?
C3A C9B 1.568(2) . ?
C4 C5 1.463(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.539(2) . ?
C5 H5 1.0000 . ?
C6 C6A 1.576(2) . ?
C6 H6 1.0000 . ?
C6A C17 1.519(2) . ?
C6A C7 1.560(2) . ?
C6A C9B 1.577(2) . ?
C7 C8 1.533(2) . ?
C7 H7 1.0000 . ?
C8 C9 1.460(2) . ?
C8 H8 1.0000 . ?
C9 C9A 1.534(2) . ?
C9 H9 1.0000 . ?
C9A C9B 1.582(2) . ?
C9B C19 1.518(2) . ?
C10 C11 1.504(2) . ?
C11 C16 1.393(2) . ?
C11 C12 1.394(2) . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
Cl1 C21 1.7644(17) . ?
Cl2 C21 1.7660(16) . ?
Cl3 C21 1.7657(18) . ?
C21 H21 1.0000 . ?

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
C4 O1 C5 60.95(9) . . ?
C6 O2 C3A 98.39(10) . . ?
C9A O3 C7 98.62(10) . . ?
C9 O4 C8 61.04(9) . . ?
C17 O7 C18 115.58(13) . . ?
C19 O9 C20 114.49(12) . . ?
N2 C1 C9A 109.94(12) . . ?
N2 C1 H1A 109.7 . . ?
C9A C1 H1A 109.7 . . ?
N2 C1 H1B 109.7 . . ?
C9A C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C10 N2 C3 123.14(12) . . ?
C10 N2 C1 119.74(12) . . ?
C3 N2 C1 114.62(12) . . ?
N2 C3 C3A 109.65(12) . . ?
N2 C3 H3A 109.7 . . ?
C3A C3 H3A 109.7 . . ?
N2 C3 H3B 109.7 . . ?
C3A C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
O2 C3A C3 110.18(12) . . ?
O2 C3A C4 101.41(11) . . ?
C3 C3A C4 119.02(12) . . ?
O2 C3A C9B 102.01(11) . . ?
C3 C3A C9B 115.02(12) . . ?
C4 C3A C9B 107.06(11) . . ?
O1 C4 C5 59.70(9) . . ?
O1 C4 C3A 112.19(12) . . ?
C5 C4 C3A 103.02(12) . . ?
O1 C4 H4 121.7 . . ?
C5 C4 H4 121.7 . . ?
C3A C4 H4 121.7 . . ?
O1 C5 C4 59.36(9) . . ?
O1 C5 C6 111.90(12) . . ?
C4 C5 C6 103.33(12) . . ?
O1 C5 H5 121.8 . . ?
C4 C5 H5 121.8 . . ?
C6 C5 H5 121.8 . . ?
O2 C6 C5 101.35(11) . . ?
O2 C6 C6A 102.48(11) . . ?
C5 C6 C6A 108.02(12) . . ?
O2 C6 H6 114.5 . . ?
C5 C6 H6 114.5 . . ?
C6A C6 H6 114.5 . . ?
C17 C6A C7 113.49(12) . . ?
C17 C6A C6 109.71(12) . . ?
C7 C6A C6 113.37(12) . . ?
C17 C6A C9B 119.03(12) . . ?
C7 C6A C9B 100.71(11) . . ?
C6 C6A C9B 99.71(11) . . ?
O3 C7 C8 100.97(11) . . ?
O3 C7 C6A 102.04(11) . . ?
C8 C7 C6A 108.22(12) . . ?
O3 C7 H7 114.7 . . ?
C8 C7 H7 114.7 . . ?
C6A C7 H7 114.7 . . ?
O4 C8 C9 59.35(9) . . ?
O4 C8 C7 111.69(12) . . ?
C9 C8 C7 103.82(12) . . ?
O4 C8 H8 121.7 . . ?
C9 C8 H8 121.7 . . ?
C7 C8 H8 121.7 . . ?
O4 C9 C8 59.61(9) . . ?
O4 C9 C9A 112.18(12) . . ?
C8 C9 C9A 102.89(12) . . ?
O4 C9 H9 121.7 . . ?
C8 C9 H9 121.7 . . ?
C9A C9 H9 121.7 . . ?
O3 C9A C1 110.58(12) . . ?
O3 C9A C9 101.23(11) . . ?
C1 C9A C9 119.24(12) . . ?
O3 C9A C9B 102.13(11) . . ?
C1 C9A C9B 114.68(12) . . ?
C9 C9A C9B 106.87(11) . . ?
C19 C9B C3A 116.85(12) . . ?
C19 C9B C6A 116.30(12) . . ?
C3A C9B C6A 101.76(11) . . ?
C19 C9B C9A 110.75(12) . . ?
C3A C9B C9A 108.73(11) . . ?
C6A C9B C9A 100.95(11) . . ?
O5 C10 N2 122.75(14) . . ?
O5 C10 C11 119.62(13) . . ?
N2 C10 C11 117.60(13) . . ?
C16 C11 C12 120.02(14) . . ?
C16 C11 C10 119.01(14) . . ?
C12 C11 C10 120.92(14) . . ?
C13 C12 C11 120.03(15) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 119.87(15) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.26(15) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 120.09(15) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 119.69(15) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
O6 C17 O7 123.82(14) . . ?
O6 C17 C6A 126.06(14) . . ?
O7 C17 C6A 109.92(13) . . ?
O7 C18 H18A 109.5 . . ?
O7 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O7 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O8 C19 O9 123.62(14) . . ?
O8 C19 C9B 124.40(14) . . ?
O9 C19 C9B 111.89(12) . . ?
O9 C20 H20A 109.5 . . ?
O9 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O9 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Cl1 C21 Cl3 111.01(9) . . ?
Cl1 C21 Cl2 110.11(9) . . ?
Cl3 C21 Cl2 110.17(9) . . ?
Cl1 C21 H21 108.5 . . ?
Cl3 C21 H21 108.5 . . ?
Cl2 C21 H21 108.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A C1 N2 C10 137.60(14) . . . . ?
C9A C1 N2 C3 -59.77(16) . . . . ?
C10 N2 C3 C3A -137.68(14) . . . . ?
C1 N2 C3 C3A 60.35(16) . . . . ?
C6 O2 C3A C3 -178.84(11) . . . . ?
C6 O2 C3A C4 54.19(12) . . . . ?
C6 O2 C3A C9B -56.23(12) . . . . ?
N2 C3 C3A O2 61.50(15) . . . . ?
N2 C3 C3A C4 177.91(12) . . . . ?
N2 C3 C3A C9B -53.09(16) . . . . ?
C5 O1 C4 C3A -92.49(13) . . . . ?
O2 C3A C4 O1 29.12(15) . . . . ?
C3 C3A C4 O1 -91.83(16) . . . . ?
C9B C3A C4 O1 135.61(12) . . . . ?
O2 C3A C4 C5 -33.17(14) . . . . ?
C3 C3A C4 C5 -154.12(13) . . . . ?
C9B C3A C4 C5 73.32(14) . . . . ?
C4 O1 C5 C6 92.91(13) . . . . ?
C3A C4 C5 O1 108.29(12) . . . . ?
O1 C4 C5 C6 -107.76(12) . . . . ?
C3A C4 C5 C6 0.52(14) . . . . ?
C3A O2 C6 C5 -53.65(12) . . . . ?
C3A O2 C6 C6A 57.91(12) . . . . ?
O1 C5 C6 O2 -29.48(15) . . . . ?
C4 C5 C6 O2 32.53(14) . . . . ?
O1 C5 C6 C6A -136.76(12) . . . . ?
C4 C5 C6 C6A -74.75(14) . . . . ?
O2 C6 C6A C17 -161.29(11) . . . . ?
C5 C6 C6A C17 -54.79(15) . . . . ?
O2 C6 C6A C7 70.69(14) . . . . ?
C5 C6 C6A C7 177.18(12) . . . . ?
O2 C6 C6A C9B -35.54(13) . . . . ?
C5 C6 C6A C9B 70.96(13) . . . . ?
C9A O3 C7 C8 53.39(12) . . . . ?
C9A O3 C7 C6A -58.15(12) . . . . ?
C17 C6A C7 O3 164.42(11) . . . . ?
C6 C6A C7 O3 -69.54(14) . . . . ?
C9B C6A C7 O3 36.05(13) . . . . ?
C17 C6A C7 C8 58.45(15) . . . . ?
C6 C6A C7 C8 -175.51(12) . . . . ?
C9B C6A C7 C8 -69.91(13) . . . . ?
C9 O4 C8 C7 -93.62(13) . . . . ?
O3 C7 C8 O4 30.44(14) . . . . ?
C6A C7 C8 O4 137.15(12) . . . . ?
O3 C7 C8 C9 -31.71(14) . . . . ?
C6A C7 C8 C9 75.00(14) . . . . ?
C8 O4 C9 C9A 92.31(13) . . . . ?
C7 C8 C9 O4 107.26(13) . . . . ?
O4 C8 C9 C9A -108.35(12) . . . . ?
C7 C8 C9 C9A -1.09(15) . . . . ?
C7 O3 C9A C1 178.30(11) . . . . ?
C7 O3 C9A C9 -54.36(12) . . . . ?
C7 O3 C9A C9B 55.83(12) . . . . ?
N2 C1 C9A O3 -63.25(15) . . . . ?
N2 C1 C9A C9 -179.90(12) . . . . ?
N2 C1 C9A C9B 51.55(16) . . . . ?
O4 C9 C9A O3 -28.33(15) . . . . ?
C8 C9 C9A O3 33.82(14) . . . . ?
O4 C9 C9A C1 93.12(16) . . . . ?
C8 C9 C9A C1 155.28(13) . . . . ?
O4 C9 C9A C9B -134.83(12) . . . . ?
C8 C9 C9A C9B -72.68(14) . . . . ?
O2 C3A C9B C19 160.11(11) . . . . ?
C3 C3A C9B C19 -80.65(16) . . . . ?
C4 C3A C9B C19 54.04(16) . . . . ?
O2 C3A C9B C6A 32.32(13) . . . . ?
C3 C3A C9B C6A 151.56(12) . . . . ?
C4 C3A C9B C6A -73.75(13) . . . . ?
O2 C3A C9B C9A -73.67(13) . . . . ?
C3 C3A C9B C9A 45.57(15) . . . . ?
C4 C3A C9B C9A -179.74(11) . . . . ?
C17 C6A C9B C19 -7.43(18) . . . . ?
C7 C6A C9B C19 117.24(13) . . . . ?
C6 C6A C9B C19 -126.53(12) . . . . ?
C17 C6A C9B C3A 120.71(13) . . . . ?
C7 C6A C9B C3A -114.62(11) . . . . ?
C6 C6A C9B C3A 1.61(13) . . . . ?
C17 C6A C9B C9A -127.31(13) . . . . ?
C7 C6A C9B C9A -2.64(13) . . . . ?
C6 C6A C9B C9A 113.59(11) . . . . ?
O3 C9A C9B C19 -155.38(11) . . . . ?
C1 C9A C9B C19 84.99(15) . . . . ?
C9 C9A C9B C19 -49.52(15) . . . . ?
O3 C9A C9B C3A 74.95(13) . . . . ?
C1 C9A C9B C3A -44.68(16) . . . . ?
C9 C9A C9B C3A -179.19(11) . . . . ?
O3 C9A C9B C6A -31.60(13) . . . . ?
C1 C9A C9B C6A -151.24(12) . . . . ?
C9 C9A C9B C6A 74.26(13) . . . . ?
C3 N2 C10 O5 -161.94(14) . . . . ?
C1 N2 C10 O5 -0.8(2) . . . . ?
C3 N2 C10 C11 20.0(2) . . . . ?
C1 N2 C10 C11 -178.90(13) . . . . ?
O5 C10 C11 C16 59.7(2) . . . . ?
N2 C10 C11 C16 -122.17(16) . . . . ?
O5 C10 C11 C12 -117.65(17) . . . . ?
N2 C10 C11 C12 60.5(2) . . . . ?
C16 C11 C12 C13 -0.6(2) . . . . ?
C10 C11 C12 C13 176.72(14) . . . . ?
C11 C12 C13 C14 1.7(2) . . . . ?
C12 C13 C14 C15 -0.9(2) . . . . ?
C13 C14 C15 C16 -0.9(2) . . . . ?
C14 C15 C16 C11 2.0(2) . . . . ?
C12 C11 C16 C15 -1.2(2) . . . . ?
C10 C11 C16 C15 -178.64(14) . . . . ?
C18 O7 C17 O6 1.9(2) . . . . ?
C18 O7 C17 C6A 177.13(13) . . . . ?
C7 C6A C17 O6 -165.83(15) . . . . ?
C6 C6A C17 O6 66.21(19) . . . . ?
C9B C6A C17 O6 -47.6(2) . . . . ?
C7 C6A C17 O7 19.08(17) . . . . ?
C6 C6A C17 O7 -108.88(13) . . . . ?
C9B C6A C17 O7 137.30(13) . . . . ?
C20 O9 C19 O8 3.1(2) . . . . ?
C20 O9 C19 C9B 179.62(12) . . . . ?
C3A C9B C19 O8 -160.36(15) . . . . ?
C6A C9B C19 O8 -40.0(2) . . . . ?
C9A C9B C19 O8 74.43(18) . . . . ?
C3A C9B C19 O9 23.13(17) . . . . ?
C6A C9B C19 O9 143.47(12) . . . . ?
C9A C9B C19 O9 -102.09(14) . . . . ?

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
C7 H7 O3 1.00 2.37 3.021(2) 122 5_666
C20 H20A O5 0.98 2.37 3.333(2) 168 4_456
C21 H21 O5 1.00 2.21 3.192(2) 168 2_565

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.079

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_13a
_database_code_depnum_ccdc_archive 'CCDC 2089294'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H24 O7'
_chemical_formula_sum            'C20 H24 O7'
_chemical_formula_weight         376.39

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'
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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   8.4126(3)
_cell_length_b                   28.9949(10)
_cell_length_c                   15.4762(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.460(2)
_cell_angle_gamma                90
_cell_volume                     3771.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9633
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      32.63

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       '/f and /w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            115864
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.089
_diffrn_reflns_theta_max         32.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             13623
_reflns_number_gt                11475
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0548P)²+1.1714P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13623
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
O1 O 0.30822(8) 0.19376(2) 0.32059(4) 0.01647(12) Uani 1 1 d . . . . .
O4 O 0.33412(7) 0.23981(2) 0.54543(4) 0.01310(11) Uani 1 1 d . . . . .
O6 O 0.25649(8) 0.28944(2) 0.37833(4) 0.01629(12) Uani 1 1 d . . . . .
O8 O 0.56351(8) 0.12853(2) 0.37522(4) 0.01712(12) Uani 1 1 d . . . . .
O9 O 0.51522(8) 0.10531(2) 0.50998(4) 0.01811(13) Uani 1 1 d . . . . .
O10 O 0.74487(8) 0.25605(2) 0.38853(5) 0.02096(14) Uani 1 1 d . . . . .
O11 O 0.75688(8) 0.19384(2) 0.47524(4) 0.01796(13) Uani 1 1 d . . . . .
O21 O 0.52063(7) 0.59851(2) 0.66606(4) 0.01340(11) Uani 1 1 d . . . . .
O24 O 0.60461(7) 0.47773(2) 0.58729(4) 0.01368(11) Uani 1 1 d . . . . .
O26 O 0.81072(8) 0.56333(2) 0.58506(4) 0.01745(12) Uani 1 1 d . . . . .
O28 O 0.33135(8) 0.55500(2) 0.79683(4) 0.01574(12) Uani 1 1 d . . . . .
O29 O 0.19161(8) 0.49859(2) 0.72932(4) 0.01747(12) Uani 1 1 d . . . . .
O30 O 0.77175(8) 0.51696(2) 0.84730(4) 0.01641(12) Uani 1 1 d . . . . .
O31 O 0.53495(8) 0.48136(2) 0.84062(4) 0.01785(13) Uani 1 1 d . . . . .
C2A C 0.42001(10) 0.17987(3) 0.46123(5) 0.01108(13) Uani 1 1 d . . . . .
C2 C 0.26445(10) 0.17806(3) 0.40305(5) 0.01291(14) Uani 1 1 d . . . . .
H2A H 0.185639 0.200106 0.426462 0.015 Uiso 1 1 calc R U . . .
C3 C 0.37313(10) 0.19166(3) 0.55331(5) 0.01197(13) Uani 1 1 d . . . . .
H3A H 0.273740 0.174354 0.565477 0.014 Uiso 1 1 calc R U . . .
C4A C 0.44561(10) 0.26263(3) 0.49293(5) 0.01272(14) Uani 1 1 d . . . . .
C5 C 0.35563(11) 0.30301(3) 0.44994(6) 0.01598(15) Uani 1 1 d . . . . .
H5A H 0.289733 0.318115 0.493237 0.019 Uiso 1 1 calc R U . . .
H5B H 0.433525 0.325973 0.430513 0.019 Uiso 1 1 calc R U . . .
C7B C 0.50046(10) 0.22389(3) 0.42602(5) 0.01181(13) Uani 1 1 d . . . . .
C7 C 0.35425(11) 0.27538(3) 0.31054(6) 0.01723(16) Uani 1 1 d . . . . .
H7A H 0.438660 0.298668 0.303190 0.021 Uiso 1 1 calc R U . . .
H7B H 0.289194 0.273704 0.255790 0.021 Uiso 1 1 calc R U . . .
C7A C 0.43071(10) 0.22856(3) 0.32900(5) 0.01459(14) Uani 1 1 d . . . . .
C8 C 0.18874(11) 0.13152(3) 0.39438(6) 0.01583(15) Uani 1 1 d . . . . .
H8A H 0.237386 0.109057 0.359478 0.019 Uiso 1 1 calc R U . . .
C9 C 0.05691(12) 0.12020(3) 0.43318(7) 0.02251(18) Uani 1 1 d . . . . .
H9A H 0.006168 0.142102 0.468408 0.027 Uiso 1 1 calc R U . . .
H9B H 0.013122 0.090190 0.425782 0.027 Uiso 1 1 calc R U . . .
C10 C 0.49420(11) 0.18222(3) 0.62555(5) 0.01522(15) Uani 1 1 d . . . . .
H10A H 0.604229 0.184764 0.614914 0.018 Uiso 1 1 calc R U . . .
C11 C 0.45028(13) 0.17042(4) 0.70368(6) 0.02198(18) Uani 1 1 d . . . . .
H11A H 0.340534 0.167780 0.714959 0.026 Uiso 1 1 calc R U . . .
H11B H 0.528512 0.164595 0.748443 0.026 Uiso 1 1 calc R U . . .
C12 C 0.57845(11) 0.28432(3) 0.54881(6) 0.01847(16) Uani 1 1 d . . . . .
H12A H 0.671496 0.294171 0.521418 0.022 Uiso 1 1 calc R U . . .
C13 C 0.57216(14) 0.29030(4) 0.63340(7) 0.0251(2) Uani 1 1 d . . . . .
H13A H 0.480668 0.280795 0.662603 0.030 Uiso 1 1 calc R U . . .
H13B H 0.659148 0.304094 0.664900 0.030 Uiso 1 1 calc R U . . .
C14 C 0.54584(12) 0.21577(4) 0.26034(6) 0.02174(18) Uani 1 1 d . . . . .
H14A H 0.615082 0.190491 0.272540 0.026 Uiso 1 1 calc R U . . .
C15 C 0.55870(17) 0.23652(5) 0.18519(8) 0.0348(3) Uani 1 1 d . . . . .
H15A H 0.491909 0.261957 0.170192 0.042 Uiso 1 1 calc R U . . .
H15B H 0.634751 0.226032 0.146022 0.042 Uiso 1 1 calc R U . . .
C16 C 0.50786(10) 0.13437(3) 0.45414(5) 0.01282(14) Uani 1 1 d . . . . .
C17 C 0.64033(12) 0.08488(3) 0.35989(7) 0.02139(18) Uani 1 1 d . . . . .
H17A H 0.676562 0.084090 0.300568 0.032 Uiso 1 1 calc R U . . .
H17B H 0.731859 0.081229 0.400662 0.032 Uiso 1 1 calc R U . . .
H17C H 0.564673 0.059712 0.368060 0.032 Uiso 1 1 calc R U . . .
C18 C 0.68078(10) 0.22164(3) 0.43266(6) 0.01457(15) Uani 1 1 d . . . . .
C19 C 0.91717(12) 0.25726(4) 0.39192(8) 0.0276(2) Uani 1 1 d . . . . .
H19A H 0.953430 0.283468 0.357959 0.041 Uiso 1 1 calc R U . . .
H19B H 0.956509 0.260594 0.452124 0.041 Uiso 1 1 calc R U . . .
H19C H 0.958147 0.228545 0.367979 0.041 Uiso 1 1 calc R U . . .
C22A C 0.44616(9) 0.52024(3) 0.67616(5) 0.01104(13) Uani 1 1 d . . . . .
C22 C 0.43851(10) 0.56392(3) 0.61745(5) 0.01229(14) Uani 1 1 d . . . . .
H22A H 0.498476 0.557463 0.564370 0.015 Uiso 1 1 calc R U . . .
C23 C 0.44604(10) 0.47687(3) 0.61903(5) 0.01273(14) Uani 1 1 d . . . . .
H23A H 0.368681 0.481726 0.568978 0.015 Uiso 1 1 calc R U . . .
C24A C 0.71719(10) 0.49221(3) 0.65383(5) 0.01333(14) Uani 1 1 d . . . . .
C25 C 0.84985(11) 0.51728(3) 0.60805(6) 0.01722(16) Uani 1 1 d . . . . .
H25A H 0.947025 0.517427 0.646471 0.021 Uiso 1 1 calc R U . . .
H25B H 0.874230 0.499978 0.555086 0.021 Uiso 1 1 calc R U . . .
C27A C 0.65549(10) 0.57876(3) 0.71232(5) 0.01246(14) Uani 1 1 d . . . . .
C27 C 0.80381(10) 0.58945(3) 0.66207(6) 0.01566(15) Uani 1 1 d . . . . .
H27A H 0.804568 0.622681 0.647407 0.019 Uiso 1 1 calc R U . . .
H27B H 0.899724 0.582933 0.699371 0.019 Uiso 1 1 calc R U . . .
C27B C 0.61802(10) 0.52465(3) 0.71650(5) 0.01113(13) Uani 1 1 d . . . . .
C28 C 0.27465(11) 0.57970(3) 0.59024(5) 0.01585(15) Uani 1 1 d . . . . .
H28A H 0.207655 0.558266 0.559832 0.019 Uiso 1 1 calc R U . . .
C29 C 0.21533(12) 0.62114(3) 0.60510(6) 0.02098(17) Uani 1 1 d . . . . .
H29A H 0.278433 0.643584 0.635301 0.025 Uiso 1 1 calc R U . . .
H29B H 0.109706 0.628408 0.585548 0.025 Uiso 1 1 calc R U . . .
C30 C 0.40808(11) 0.43160(3) 0.66113(6) 0.01603(15) Uani 1 1 d . . . . .
H30A H 0.454067 0.424869 0.716840 0.019 Uiso 1 1 calc R U . . .
C31 C 0.31228(14) 0.40090(3) 0.62261(7) 0.02432(19) Uani 1 1 d . . . . .
H31A H 0.265465 0.407180 0.566896 0.029 Uiso 1 1 calc R U . . .
H31B H 0.290422 0.372614 0.650704 0.029 Uiso 1 1 calc R U . . .
C32 C 0.79774(11) 0.45096(3) 0.69740(6) 0.01829(16) Uani 1 1 d . . . . .
H32A H 0.859450 0.456269 0.749299 0.022 Uiso 1 1 calc R U . . .
C33 C 0.78801(13) 0.40810(3) 0.66813(7) 0.02319(19) Uani 1 1 d . . . . .
H33A H 0.727335 0.401510 0.616421 0.028 Uiso 1 1 calc R U . . .
H33B H 0.841706 0.383931 0.698849 0.028 Uiso 1 1 calc R U . . .
C34 C 0.67607(11) 0.60375(3) 0.79821(5) 0.01566(15) Uani 1 1 d . . . . .
H34A H 0.772086 0.598617 0.831380 0.019 Uiso 1 1 calc R U . . .
C35 C 0.57051(12) 0.63218(3) 0.83059(6) 0.01989(17) Uani 1 1 d . . . . .
H35A H 0.473011 0.638206 0.799388 0.024 Uiso 1 1 calc R U . . .
H35B H 0.592359 0.646523 0.884999 0.024 Uiso 1 1 calc R U . . .
C36 C 0.30994(10) 0.52204(3) 0.73714(5) 0.01235(14) Uani 1 1 d . . . . .
C37 C 0.20829(12) 0.55859(3) 0.85831(6) 0.02073(17) Uani 1 1 d . . . . .
H37A H 0.234307 0.583547 0.899211 0.031 Uiso 1 1 calc R U . . .
H37B H 0.106462 0.565230 0.827711 0.031 Uiso 1 1 calc R U . . .
H37C H 0.200342 0.529431 0.889858 0.031 Uiso 1 1 calc R U . . .
C38 C 0.63276(10) 0.50528(3) 0.80793(5) 0.01275(14) Uani 1 1 d . . . . .
C39 C 0.79089(13) 0.50337(3) 0.93704(6) 0.02092(18) Uani 1 1 d . . . . .
H39A H 0.895541 0.513323 0.960261 0.031 Uiso 1 1 calc R U . . .
H39B H 0.707606 0.517837 0.970166 0.031 Uiso 1 1 calc R U . . .
H39C H 0.782479 0.469755 0.941503 0.031 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.4182(10) . ?
O1 C7A 1.4441(11) . ?
O4 C4A 1.4294(10) . ?
O4 C3 1.4380(10) . ?
O6 C5 1.4138(11) . ?
O6 C7 1.4204(11) . ?
O8 C16 1.3375(10) . ?
O8 C17 1.4453(11) . ?
O9 C16 1.2067(10) . ?
O10 C18 1.3358(10) . ?
O10 C19 1.4486(12) . ?
O11 C18 1.2074(10) . ?
O21 C22 1.4158(10) . ?
O21 C27A 1.4344(10) . ?
O24 C24A 1.4318(10) . ?
O24 C23 1.4413(10) . ?
O26 C27 1.4154(11) . ?
O26 C25 1.4169(12) . ?
O28 C36 1.3359(10) . ?
O28 C37 1.4396(11) . ?
O29 C36 1.2073(10) . ?
O30 C38 1.3386(10) . ?
O30 C39 1.4458(11) . ?
O31 C38 1.2040(11) . ?
C2A C16 1.5184(11) . ?
C2A C3 1.5335(11) . ?
C2A C7B 1.5543(11) . ?
C2A C2 1.5572(12) . ?
C2 C8 1.4958(12) . ?
C2 H2A 1.0000 . ?
C3 C10 1.5048(12) . ?
C3 H3A 1.0000 . ?
C4A C12 1.5196(12) . ?
C4A C5 1.5308(12) . ?
C4A C7B 1.6087(12) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7B C18 1.5174(12) . ?
C7B C7A 1.5943(12) . ?
C7 C7A 1.5240(12) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7A C14 1.5143(13) . ?
C8 C9 1.3249(13) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
C9 H9B 0.9500 . ?
C10 C11 1.3243(12) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C11 H11B 0.9500 . ?
C12 C13 1.3239(14) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C13 H13B 0.9500 . ?
C14 C15 1.3180(14) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C15 H15B 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C22A C36 1.5165(11) . ?
C22A C23 1.5372(11) . ?
C22A C27B 1.5553(11) . ?
C22A C22 1.5582(11) . ?
C22 C28 1.4958(12) . ?
C22 H22A 1.0000 . ?
C23 C30 1.5058(12) . ?
C23 H23A 1.0000 . ?
C24A C32 1.5184(12) . ?
C24A C25 1.5309(12) . ?
C24A C27B 1.6096(12) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C27A C34 1.5173(12) . ?
C27A C27 1.5300(12) . ?
C27A C27B 1.6022(11) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27B C38 1.5226(11) . ?
C28 C29 1.3250(13) . ?
C28 H28A 0.9500 . ?
C29 H29A 0.9500 . ?
C29 H29B 0.9500 . ?
C30 C31 1.3252(13) . ?
C30 H30A 0.9500 . ?
C31 H31A 0.9500 . ?
C31 H31B 0.9500 . ?
C32 C33 1.3240(14) . ?
C32 H32A 0.9500 . ?
C33 H33A 0.9500 . ?
C33 H33B 0.9500 . ?
C34 C35 1.3257(13) . ?
C34 H34A 0.9500 . ?
C35 H35A 0.9500 . ?
C35 H35B 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C7A 110.79(6) . . ?
C4A O4 C3 110.16(6) . . ?
C5 O6 C7 108.54(7) . . ?
C16 O8 C17 115.94(7) . . ?
C18 O10 C19 115.14(7) . . ?
C22 O21 C27A 109.87(6) . . ?
C24A O24 C23 110.69(6) . . ?
C27 O26 C25 108.08(7) . . ?
C36 O28 C37 115.42(7) . . ?
C38 O30 C39 115.30(7) . . ?
C16 C2A C3 113.97(6) . . ?
C16 C2A C7B 117.87(7) . . ?
C3 C2A C7B 106.01(6) . . ?
C16 C2A C2 109.18(7) . . ?
C3 C2A C2 107.56(6) . . ?
C7B C2A C2 101.11(6) . . ?
O1 C2 C8 109.57(7) . . ?
O1 C2 C2A 105.38(6) . . ?
C8 C2 C2A 115.23(7) . . ?
O1 C2 H2A 108.8 . . ?
C8 C2 H2A 108.8 . . ?
C2A C2 H2A 108.8 . . ?
O4 C3 C10 112.61(7) . . ?
O4 C3 C2A 101.80(6) . . ?
C10 C3 C2A 117.20(7) . . ?
O4 C3 H3A 108.3 . . ?
C10 C3 H3A 108.3 . . ?
C2A C3 H3A 108.3 . . ?
O4 C4A C12 110.65(7) . . ?
O4 C4A C5 106.07(7) . . ?
C12 C4A C5 105.59(7) . . ?
O4 C4A C7B 104.83(6) . . ?
C12 C4A C7B 115.53(7) . . ?
C5 C4A C7B 113.85(7) . . ?
O6 C5 C4A 113.08(7) . . ?
O6 C5 H5A 109.0 . . ?
C4A C5 H5A 109.0 . . ?
O6 C5 H5B 109.0 . . ?
C4A C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C18 C7B C2A 112.95(6) . . ?
C18 C7B C7A 113.19(7) . . ?
C2A C7B C7A 104.57(6) . . ?
C18 C7B C4A 107.46(7) . . ?
C2A C7B C4A 101.91(6) . . ?
C7A C7B C4A 116.29(6) . . ?
O6 C7 C7A 111.74(7) . . ?
O6 C7 H7A 109.3 . . ?
C7A C7 H7A 109.3 . . ?
O6 C7 H7B 109.3 . . ?
C7A C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
O1 C7A C14 103.95(7) . . ?
O1 C7A C7 108.16(7) . . ?
C14 C7A C7 111.36(7) . . ?
O1 C7A C7B 104.95(6) . . ?
C14 C7A C7B 114.80(7) . . ?
C7 C7A C7B 112.79(7) . . ?
C9 C8 C2 122.98(8) . . ?
C9 C8 H8A 118.5 . . ?
C2 C8 H8A 118.5 . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
C11 C10 C3 121.26(9) . . ?
C11 C10 H10A 119.4 . . ?
C3 C10 H10A 119.4 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C13 C12 C4A 123.87(9) . . ?
C13 C12 H12A 118.1 . . ?
C4A C12 H12A 118.1 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C15 C14 C7A 125.91(10) . . ?
C15 C14 H14A 117.0 . . ?
C7A C14 H14A 117.0 . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
O9 C16 O8 123.79(8) . . ?
O9 C16 C2A 124.42(8) . . ?
O8 C16 C2A 111.51(7) . . ?
O8 C17 H17A 109.5 . . ?
O8 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O8 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O11 C18 O10 124.16(8) . . ?
O11 C18 C7B 124.81(8) . . ?
O10 C18 C7B 110.95(7) . . ?
O10 C19 H19A 109.5 . . ?
O10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C36 C22A C23 113.84(7) . . ?
C36 C22A C27B 117.49(6) . . ?
C23 C22A C27B 106.01(6) . . ?
C36 C22A C22 108.75(6) . . ?
C23 C22A C22 109.30(6) . . ?
C27B C22A C22 100.47(6) . . ?
O21 C22 C28 110.83(7) . . ?
O21 C22 C22A 105.01(6) . . ?
C28 C22 C22A 115.30(7) . . ?
O21 C22 H22A 108.5 . . ?
C28 C22 H22A 108.5 . . ?
C22A C22 H22A 108.5 . . ?
O24 C23 C30 112.27(7) . . ?
O24 C23 C22A 101.78(6) . . ?
C30 C23 C22A 117.33(7) . . ?
O24 C23 H23A 108.3 . . ?
C30 C23 H23A 108.3 . . ?
C22A C23 H23A 108.3 . . ?
O24 C24A C32 110.92(7) . . ?
O24 C24A C25 106.22(7) . . ?
C32 C24A C25 105.02(7) . . ?
O24 C24A C27B 105.12(6) . . ?
C32 C24A C27B 115.20(7) . . ?
C25 C24A C27B 114.11(7) . . ?
O26 C25 C24A 113.42(7) . . ?
O26 C25 H25A 108.9 . . ?
C24A C25 H25A 108.9 . . ?
O26 C25 H25B 108.9 . . ?
C24A C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
O21 C27A C34 107.74(7) . . ?
O21 C27A C27 108.08(6) . . ?
C34 C27A C27 106.49(7) . . ?
O21 C27A C27B 104.97(6) . . ?
C34 C27A C27B 116.58(6) . . ?
C27 C27A C27B 112.64(7) . . ?
O26 C27 C27A 112.55(7) . . ?
O26 C27 H27A 109.1 . . ?
C27A C27 H27A 109.1 . . ?
O26 C27 H27B 109.1 . . ?
C27A C27 H27B 109.1 . . ?
H27A C27 H27B 107.8 . . ?
C38 C27B C22A 112.33(7) . . ?
C38 C27B C27A 112.98(6) . . ?
C22A C27B C27A 104.21(6) . . ?
C38 C27B C24A 108.71(6) . . ?
C22A C27B C24A 101.95(6) . . ?
C27A C27B C24A 116.10(6) . . ?
C29 C28 C22 125.31(9) . . ?
C29 C28 H28A 117.3 . . ?
C22 C28 H28A 117.3 . . ?
C28 C29 H29A 120.0 . . ?
C28 C29 H29B 120.0 . . ?
H29A C29 H29B 120.0 . . ?
C31 C30 C23 121.81(8) . . ?
C31 C30 H30A 119.1 . . ?
C23 C30 H30A 119.1 . . ?
C30 C31 H31A 120.0 . . ?
C30 C31 H31B 120.0 . . ?
H31A C31 H31B 120.0 . . ?
C33 C32 C24A 124.59(9) . . ?
C33 C32 H32A 117.7 . . ?
C24A C32 H32A 117.7 . . ?
C32 C33 H33A 120.0 . . ?
C32 C33 H33B 120.0 . . ?
H33A C33 H33B 120.0 . . ?
C35 C34 C27A 125.10(8) . . ?
C35 C34 H34A 117.5 . . ?
C27A C34 H34A 117.5 . . ?
C34 C35 H35A 120.0 . . ?
C34 C35 H35B 120.0 . . ?
H35A C35 H35B 120.0 . . ?
O29 C36 O28 123.94(8) . . ?
O29 C36 C22A 124.07(8) . . ?
O28 C36 C22A 111.83(7) . . ?
O28 C37 H37A 109.5 . . ?
O28 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O28 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O31 C38 O30 123.63(8) . . ?
O31 C38 C27B 124.96(8) . . ?
O30 C38 C27B 111.37(7) . . ?
O30 C39 H39A 109.5 . . ?
O30 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O30 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7A O1 C2 C8 -158.40(7) . . . . ?
C7A O1 C2 C2A -33.86(8) . . . . ?
C16 C2A C2 O1 -88.79(7) . . . . ?
C3 C2A C2 O1 147.08(6) . . . . ?
C7B C2A C2 O1 36.16(8) . . . . ?
C16 C2A C2 C8 32.12(9) . . . . ?
C3 C2A C2 C8 -92.02(8) . . . . ?
C7B C2A C2 C8 157.06(7) . . . . ?
C4A O4 C3 C10 85.65(8) . . . . ?
C4A O4 C3 C2A -40.70(8) . . . . ?
C16 C2A C3 O4 165.07(7) . . . . ?
C7B C2A C3 O4 33.78(8) . . . . ?
C2 C2A C3 O4 -73.75(7) . . . . ?
C16 C2A C3 C10 41.77(10) . . . . ?
C7B C2A C3 C10 -89.52(8) . . . . ?
C2 C2A C3 C10 162.96(7) . . . . ?
C3 O4 C4A C12 -94.72(8) . . . . ?
C3 O4 C4A C5 151.24(7) . . . . ?
C3 O4 C4A C7B 30.47(8) . . . . ?
C7 O6 C5 C4A -68.87(9) . . . . ?
O4 C4A C5 O6 -78.83(8) . . . . ?
C12 C4A C5 O6 163.69(7) . . . . ?
C7B C4A C5 O6 35.92(10) . . . . ?
C16 C2A C7B C18 -30.25(10) . . . . ?
C3 C2A C7B C18 98.79(8) . . . . ?
C2 C2A C7B C18 -149.11(7) . . . . ?
C16 C2A C7B C7A 93.26(8) . . . . ?
C3 C2A C7B C7A -137.70(7) . . . . ?
C2 C2A C7B C7A -25.60(7) . . . . ?
C16 C2A C7B C4A -145.24(7) . . . . ?
C3 C2A C7B C4A -16.19(8) . . . . ?
C2 C2A C7B C4A 95.90(7) . . . . ?
O4 C4A C7B C18 -126.09(7) . . . . ?
C12 C4A C7B C18 -4.04(9) . . . . ?
C5 C4A C7B C18 118.42(8) . . . . ?
O4 C4A C7B C2A -7.13(8) . . . . ?
C12 C4A C7B C2A 114.93(7) . . . . ?
C5 C4A C7B C2A -122.61(7) . . . . ?
O4 C4A C7B C7A 105.89(7) . . . . ?
C12 C4A C7B C7A -132.05(8) . . . . ?
C5 C4A C7B C7A -9.59(10) . . . . ?
C5 O6 C7 C7A 73.71(9) . . . . ?
C2 O1 C7A C14 137.20(7) . . . . ?
C2 O1 C7A C7 -104.34(8) . . . . ?
C2 O1 C7A C7B 16.29(9) . . . . ?
O6 C7 C7A O1 71.37(9) . . . . ?
O6 C7 C7A C14 -175.00(8) . . . . ?
O6 C7 C7A C7B -44.24(10) . . . . ?
C18 C7B C7A O1 130.93(7) . . . . ?
C2A C7B C7A O1 7.58(8) . . . . ?
C4A C7B C7A O1 -103.91(8) . . . . ?
C18 C7B C7A C14 17.46(10) . . . . ?
C2A C7B C7A C14 -105.89(8) . . . . ?
C4A C7B C7A C14 142.62(8) . . . . ?
C18 C7B C7A C7 -111.55(8) . . . . ?
C2A C7B C7A C7 125.10(7) . . . . ?
C4A C7B C7A C7 13.61(10) . . . . ?
O1 C2 C8 C9 -135.08(9) . . . . ?
C2A C2 C8 C9 106.32(10) . . . . ?
O4 C3 C10 C11 94.15(10) . . . . ?
C2A C3 C10 C11 -148.27(9) . . . . ?
O4 C4A C12 C13 -14.27(12) . . . . ?
C5 C4A C12 C13 100.08(10) . . . . ?
C7B C4A C12 C13 -133.16(9) . . . . ?
O1 C7A C14 C15 103.49(13) . . . . ?
C7 C7A C14 C15 -12.75(16) . . . . ?
C7B C7A C14 C15 -142.46(12) . . . . ?
C17 O8 C16 O9 -2.01(13) . . . . ?
C17 O8 C16 C2A -176.15(7) . . . . ?
C3 C2A C16 O9 13.81(12) . . . . ?
C7B C2A C16 O9 139.02(9) . . . . ?
C2 C2A C16 O9 -106.47(9) . . . . ?
C3 C2A C16 O8 -172.09(7) . . . . ?
C7B C2A C16 O8 -46.88(10) . . . . ?
C2 C2A C16 O8 67.63(9) . . . . ?
C19 O10 C18 O11 2.33(14) . . . . ?
C19 O10 C18 C7B 179.17(8) . . . . ?
C2A C7B C18 O11 -14.02(12) . . . . ?
C7A C7B C18 O11 -132.62(9) . . . . ?
C4A C7B C18 O11 97.59(10) . . . . ?
C2A C7B C18 O10 169.16(7) . . . . ?
C7A C7B C18 O10 50.56(10) . . . . ?
C4A C7B C18 O10 -79.23(9) . . . . ?
C27A O21 C22 C28 163.18(7) . . . . ?
C27A O21 C22 C22A 38.05(8) . . . . ?
C36 C22A C22 O21 85.37(7) . . . . ?
C23 C22A C22 O21 -149.79(6) . . . . ?
C27B C22A C22 O21 -38.58(7) . . . . ?
C36 C22A C22 C28 -36.90(9) . . . . ?
C23 C22A C22 C28 87.93(8) . . . . ?
C27B C22A C22 C28 -160.85(7) . . . . ?
C24A O24 C23 C30 -87.12(8) . . . . ?
C24A O24 C23 C22A 39.19(8) . . . . ?
C36 C22A C23 O24 -164.81(6) . . . . ?
C27B C22A C23 O24 -34.13(7) . . . . ?
C22 C22A C23 O24 73.37(7) . . . . ?
C36 C22A C23 C30 -41.89(10) . . . . ?
C27B C22A C23 C30 88.80(8) . . . . ?
C22 C22A C23 C30 -163.70(7) . . . . ?
C23 O24 C24A C32 97.29(8) . . . . ?
C23 O24 C24A C25 -149.12(7) . . . . ?
C23 O24 C24A C27B -27.84(8) . . . . ?
C27 O26 C25 C24A 68.76(9) . . . . ?
O24 C24A C25 O26 79.89(8) . . . . ?
C32 C24A C25 O26 -162.52(7) . . . . ?
C27B C24A C25 O26 -35.42(10) . . . . ?
C22 O21 C27A C34 -145.13(7) . . . . ?
C22 O21 C27A C27 100.17(7) . . . . ?
C22 O21 C27A C27B -20.26(8) . . . . ?
C25 O26 C27 C27A -73.34(9) . . . . ?
O21 C27A C27 O26 -72.40(9) . . . . ?
C34 C27A C27 O26 172.07(7) . . . . ?
C27B C27A C27 O26 43.10(9) . . . . ?
C36 C22A C27B C38 30.42(10) . . . . ?
C23 C22A C27B C38 -98.15(7) . . . . ?
C22 C22A C27B C38 148.11(7) . . . . ?
C36 C22A C27B C27A -92.23(8) . . . . ?
C23 C22A C27B C27A 139.21(6) . . . . ?
C22 C22A C27B C27A 25.46(7) . . . . ?
C36 C22A C27B C24A 146.61(7) . . . . ?
C23 C22A C27B C24A 18.04(8) . . . . ?
C22 C22A C27B C24A -95.70(7) . . . . ?
O21 C27A C27B C38 -127.49(7) . . . . ?
C34 C27A C27B C38 -8.39(10) . . . . ?
C27 C27A C27B C38 115.15(8) . . . . ?
O21 C27A C27B C22A -5.27(8) . . . . ?
C34 C27A C27B C22A 113.83(8) . . . . ?
C27 C27A C27B C22A -122.63(7) . . . . ?
O21 C27A C27B C24A 105.94(7) . . . . ?
C34 C27A C27B C24A -134.96(7) . . . . ?
C27 C27A C27B C24A -11.42(9) . . . . ?
O24 C24A C27B C38 123.27(7) . . . . ?
C32 C24A C27B C38 0.86(10) . . . . ?
C25 C24A C27B C38 -120.77(8) . . . . ?
O24 C24A C27B C22A 4.47(8) . . . . ?
C32 C24A C27B C22A -117.94(8) . . . . ?
C25 C24A C27B C22A 120.43(7) . . . . ?
O24 C24A C27B C27A -108.05(7) . . . . ?
C32 C24A C27B C27A 129.54(8) . . . . ?
C25 C24A C27B C27A 7.91(10) . . . . ?
O21 C22 C28 C29 3.30(12) . . . . ?
C22A C22 C28 C29 122.40(10) . . . . ?
O24 C23 C30 C31 -105.67(10) . . . . ?
C22A C23 C30 C31 136.95(10) . . . . ?
O24 C24A C32 C33 11.57(13) . . . . ?
C25 C24A C32 C33 -102.77(11) . . . . ?
C27B C24A C32 C33 130.81(10) . . . . ?
O21 C27A C34 C35 11.71(11) . . . . ?
C27 C27A C34 C35 127.46(9) . . . . ?
C27B C27A C34 C35 -105.89(10) . . . . ?
C37 O28 C36 O29 5.43(12) . . . . ?
C37 O28 C36 C22A -179.08(7) . . . . ?
C23 C22A C36 O29 -16.90(11) . . . . ?
C27B C22A C36 O29 -141.65(8) . . . . ?
C22 C22A C36 O29 105.22(9) . . . . ?
C23 C22A C36 O28 167.62(7) . . . . ?
C27B C22A C36 O28 42.87(9) . . . . ?
C22 C22A C36 O28 -70.27(8) . . . . ?
C39 O30 C38 O31 -6.98(12) . . . . ?
C39 O30 C38 C27B 175.01(7) . . . . ?
C22A C27B C38 O31 13.61(12) . . . . ?
C27A C27B C38 O31 131.15(9) . . . . ?
C24A C27B C38 O31 -98.44(10) . . . . ?
C22A C27B C38 O30 -168.41(7) . . . . ?
C27A C27B C38 O30 -50.86(9) . . . . ?
C24A C27B C38 O30 79.54(8) . . . . ?

_refine_diff_density_max         0.462
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.051



# start Validation Reply Form
_vrf_PLAT910_13a                 
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 31 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_11c
_database_code_depnum_ccdc_archive 'CCDC 2089293'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H19 N O7'
_chemical_formula_sum            'C22 H19 N O7'
_chemical_formula_weight         409.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0034 '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 0.0130 0.0069 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0220 0.0125 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   18.195(4)
_cell_length_b                   30.110(6)
_cell_length_c                   20.480(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.85(3)
_cell_angle_gamma                90
_cell_volume                     10981(4)
_cell_formula_units_Z            24
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      3.5
_cell_measurement_theta_max      30.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_F_000             5136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.250
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_process_details   'Scala (Evans, 2005)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.98700
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            188156
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_av_R_equivalents  0.1049
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.391
_diffrn_reflns_theta_max         38.388
_diffrn_reflns_theta_full        36.313
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measured_fraction_theta_full 0.937
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_Laue_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_point_group_measured_fraction_full 0.937
_reflns_number_total             20234
_reflns_number_gt                14815
_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       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  SHELXTL

_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)+(0.08P)²+20P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         20234
_refine_ls_number_parameters     1627
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0751
_refine_ls_wR_factor_ref         0.1993
_refine_ls_wR_factor_gt          0.1754
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56441(10) 0.07688(7) 0.35682(9) 0.0210(4) Uani 1 1 d . . . . .
O2 O 0.59725(10) 0.09152(7) 0.24254(9) 0.0202(4) Uani 1 1 d . . . . .
O3 O 0.64430(13) -0.04561(8) 0.24620(13) 0.0388(6) Uani 1 1 d . . . . .
O4 O 0.54580(11) -0.05120(7) 0.29463(10) 0.0254(5) Uani 1 1 d . . . . .
H4O H 0.5556 -0.0806 0.2906 0.038 Uiso 1 1 d R U . . .
O5 O 0.62340(15) 0.19620(8) 0.29415(11) 0.0389(6) Uani 1 1 d . . . . .
O6 O 0.74035(12) -0.01802(8) 0.37465(12) 0.0376(6) Uani 1 1 d . . . . .
O7 O 0.80086(10) 0.03932(7) 0.33936(10) 0.0252(5) Uani 1 1 d . . . . .
C1 C 0.64138(15) 0.06650(10) 0.38586(14) 0.0213(6) Uani 1 1 d . . . . .
C2 C 0.63126(16) 0.02854(11) 0.43216(14) 0.0244(7) Uani 1 1 d . . . . .
H2 H 0.6623 0.0215 0.4741 0.029 Uiso 1 1 calc R U . . .
C3 C 0.56977(16) 0.00727(11) 0.40155(14) 0.0231(7) Uani 1 1 d . . . . .
H3 H 0.5478 -0.0182 0.4172 0.028 Uiso 1 1 calc R U . . .
C4 C 0.54173(15) 0.03197(10) 0.33646(14) 0.0228(7) Uani 1 1 d . . . . .
H4 H 0.4870 0.0282 0.3169 0.027 Uiso 1 1 calc R U . . .
C5 C 0.59564(15) 0.02042(10) 0.28814(14) 0.0195(6) Uani 1 1 d . . . . .
C6 C 0.57762(15) 0.04671(10) 0.22030(14) 0.0214(6) Uani 1 1 d . . . . .
H6 H 0.5253 0.0430 0.1939 0.026 Uiso 1 1 calc R U . . .
C7 C 0.63945(16) 0.03716(11) 0.18198(14) 0.0236(7) Uani 1 1 d . . . . .
H7 H 0.6358 0.0187 0.1439 0.028 Uiso 1 1 calc R U . . .
C8 C 0.69937(16) 0.05975(10) 0.21239(14) 0.0222(6) Uani 1 1 d . . . . .
H8 H 0.7470 0.0613 0.2002 0.027 Uiso 1 1 calc R U . . .
C9 C 0.67546(14) 0.08271(10) 0.27114(13) 0.0197(6) Uani 1 1 d . . . . .
C10 C 0.71444(16) 0.12415(10) 0.30116(14) 0.0220(6) Uani 1 1 d . . . . .
H10A H 0.7686 0.1180 0.3173 0.026 Uiso 1 1 calc R U . . .
H10B H 0.7096 0.1476 0.2666 0.026 Uiso 1 1 calc R U . . .
N11 N 0.68185(13) 0.13997(8) 0.35697(11) 0.0216(5) Uani 1 1 d . . . . .
C12 C 0.68369(16) 0.10828(10) 0.41133(14) 0.0225(6) Uani 1 1 d . . . . .
H12A H 0.6608 0.1219 0.4464 0.027 Uiso 1 1 calc R U . . .
H12B H 0.7365 0.1007 0.4314 0.027 Uiso 1 1 calc R U . . .
C13 C 0.66832(14) 0.04522(10) 0.32344(14) 0.0184(6) Uani 1 1 d . . . . .
C14 C 0.59997(15) -0.02871(10) 0.27469(14) 0.0223(7) Uani 1 1 d . . . . .
C15 C 0.63685(17) 0.17606(11) 0.34808(14) 0.0242(7) Uani 1 1 d . . . . .
C16 C 0.60772(16) 0.19390(10) 0.40602(14) 0.0227(7) Uani 1 1 d . . . . .
C17 C 0.65283(17) 0.22240(12) 0.44959(15) 0.0313(8) Uani 1 1 d . . . . .
H17 H 0.7024 0.2285 0.4441 0.038 Uiso 1 1 calc R U . . .
C18 C 0.62620(19) 0.24211(12) 0.50141(15) 0.0353(8) Uani 1 1 d . . . . .
H18 H 0.6577 0.2613 0.5317 0.042 Uiso 1 1 calc R U . . .
C19 C 0.55404(19) 0.23371(12) 0.50878(15) 0.0335(8) Uani 1 1 d . . . . .
H19 H 0.5354 0.2473 0.5440 0.040 Uiso 1 1 calc R U . . .
C20 C 0.5089(2) 0.20558(14) 0.46510(18) 0.0450(10) Uani 1 1 d . . . . .
H20 H 0.4590 0.1999 0.4701 0.054 Uiso 1 1 calc R U . . .
C21 C 0.5359(2) 0.18537(14) 0.41354(18) 0.0437(10) Uani 1 1 d . . . . .
H21 H 0.5046 0.1658 0.3837 0.052 Uiso 1 1 calc R U . . .
C22 C 0.73842(15) 0.01771(11) 0.34760(14) 0.0238(7) Uani 1 1 d . . . . .
C23 C 0.87156(15) 0.01656(11) 0.36292(15) 0.0273(7) Uani 1 1 d . . . . .
H23A H 0.9111 0.0311 0.3447 0.041 Uiso 1 1 calc R U . . .
H23B H 0.8669 -0.0145 0.3483 0.041 Uiso 1 1 calc R U . . .
H23C H 0.8845 0.0177 0.4118 0.041 Uiso 1 1 calc R U . . .
O8 O 0.55540(10) 0.40545(7) 0.35226(9) 0.0216(5) Uani 1 1 d . . . . .
O9 O 0.58760(10) 0.42453(7) 0.23886(9) 0.0201(4) Uani 1 1 d . . . . .
O10 O 0.63908(12) 0.29101(7) 0.22488(11) 0.0329(5) Uani 1 1 d . . . . .
O11 O 0.57154(12) 0.27599(7) 0.30069(10) 0.0286(5) Uani 1 1 d . . . . .
H11O H 0.5820 0.2482 0.2879 0.043 Uiso 1 1 d R U . . .
O12 O 0.60793(11) 0.53422(7) 0.29462(10) 0.0261(5) Uani 1 1 d . . . . .
O13 O 0.74277(13) 0.31674(9) 0.35503(14) 0.0440(7) Uani 1 1 d . . . . .
O14 O 0.79578(11) 0.38205(8) 0.34417(12) 0.0362(6) Uani 1 1 d . . . . .
C24 C 0.63334(15) 0.39913(10) 0.38080(13) 0.0207(6) Uani 1 1 d . . . . .
C25 C 0.62982(16) 0.36035(11) 0.42796(14) 0.0255(7) Uani 1 1 d . . . . .
H25 H 0.6618 0.3548 0.4700 0.031 Uiso 1 1 calc R U . . .
C26 C 0.57198(16) 0.33611(11) 0.39716(14) 0.0227(7) Uani 1 1 d . . . . .
H26 H 0.5542 0.3093 0.4129 0.027 Uiso 1 1 calc R U . . .
C27 C 0.53976(16) 0.35961(10) 0.33178(14) 0.0227(7) Uani 1 1 d . . . . .
H27 H 0.4858 0.3529 0.3126 0.027 Uiso 1 1 calc R U . . .
C28 C 0.59485(15) 0.35230(10) 0.28268(13) 0.0206(6) Uani 1 1 d . . . . .
C29 C 0.57445(15) 0.37926(10) 0.21557(14) 0.0203(6) Uani 1 1 d . . . . .
H29 H 0.5231 0.3734 0.1885 0.024 Uiso 1 1 calc R U . . .
C30 C 0.63808(15) 0.37385(10) 0.17784(14) 0.0218(6) Uani 1 1 d . . . . .
H30 H 0.6375 0.3561 0.1394 0.026 Uiso 1 1 calc R U . . .
C31 C 0.69455(15) 0.39900(10) 0.20966(14) 0.0213(6) Uani 1 1 d . . . . .
H31 H 0.7421 0.4033 0.1984 0.026 Uiso 1 1 calc R U . . .
C32 C 0.66627(14) 0.41927(10) 0.26801(13) 0.0200(6) Uani 1 1 d . . . . .
C33 C 0.69912(15) 0.46199(10) 0.29852(14) 0.0224(7) Uani 1 1 d . . . . .
H33A H 0.7538 0.4583 0.3152 0.027 Uiso 1 1 calc R U . . .
H33B H 0.6915 0.4856 0.2641 0.027 Uiso 1 1 calc R U . . .
N34 N 0.66381(13) 0.47548(8) 0.35400(11) 0.0222(6) Uani 1 1 d . . . . .
C35 C 0.66817(16) 0.44283(11) 0.40754(14) 0.0248(7) Uani 1 1 d . . . . .
H35A H 0.6416 0.4544 0.4416 0.030 Uiso 1 1 calc R U . . .
H35B H 0.7214 0.4380 0.4292 0.030 Uiso 1 1 calc R U . . .
C36 C 0.66373(14) 0.38039(10) 0.31914(13) 0.0189(6) Uani 1 1 d . . . . .
C37 C 0.60591(15) 0.30344(10) 0.26709(14) 0.0205(6) Uani 1 1 d . . . . .
C38 C 0.62030(15) 0.51236(10) 0.34751(14) 0.0211(6) Uani 1 1 d . . . . .
C39 C 0.58995(16) 0.52838(11) 0.40605(14) 0.0253(7) Uani 1 1 d . . . . .
C40 C 0.63785(18) 0.53770(12) 0.46685(15) 0.0317(8) Uani 1 1 d . . . . .
H40 H 0.6901 0.5319 0.4725 0.038 Uiso 1 1 calc R U . . .
C41 C 0.6096(2) 0.55540(12) 0.51891(16) 0.0356(8) Uani 1 1 d . . . . .
H41 H 0.6425 0.5622 0.5600 0.043 Uiso 1 1 calc R U . . .
C42 C 0.5330(2) 0.56323(12) 0.51111(17) 0.0370(8) Uani 1 1 d . . . . .
H42 H 0.5132 0.5747 0.5471 0.044 Uiso 1 1 calc R U . . .
C43 C 0.48551(19) 0.55415(12) 0.45032(18) 0.0360(8) Uani 1 1 d . . . . .
H43 H 0.4331 0.5595 0.4449 0.043 Uiso 1 1 calc R U . . .
C44 C 0.51392(17) 0.53734(11) 0.39730(16) 0.0301(7) Uani 1 1 d . . . . .
H44 H 0.4814 0.5320 0.3554 0.036 Uiso 1 1 calc R U . . .
C45 C 0.73714(15) 0.35559(11) 0.34084(14) 0.0220(7) Uani 1 1 d . . . . .
C46 C 0.86976(16) 0.36197(13) 0.36020(17) 0.0352(8) Uani 1 1 d . . . . .
H46A H 0.9054 0.3804 0.3423 0.053 Uiso 1 1 calc R U . . .
H46B H 0.8678 0.3323 0.3404 0.053 Uiso 1 1 calc R U . . .
H46C H 0.8861 0.3597 0.4087 0.053 Uiso 1 1 calc R U . . .
O15 O 0.57461(10) 0.74650(7) 0.39582(9) 0.0209(5) Uani 1 1 d . . . . .
O16 O 0.59108(10) 0.75762(7) 0.27520(9) 0.0190(4) Uani 1 1 d . . . . .
O17 O 0.68966(11) 0.62408(7) 0.37217(11) 0.0310(5) Uani 1 1 d . . . . .
O18 O 0.59060(12) 0.62089(8) 0.28635(11) 0.0322(5) Uani 1 1 d . . . . .
H18O H 0.6006 0.5913 0.2923 0.048 Uiso 1 1 d R U . . .
O19 O 0.58257(11) 0.86495(7) 0.30182(9) 0.0257(5) Uani 1 1 d . . . . .
O20 O 0.80345(11) 0.72901(8) 0.43267(10) 0.0286(5) Uani 1 1 d . . . . .
O21 O 0.79374(10) 0.68943(7) 0.33941(10) 0.0253(5) Uani 1 1 d . . . . .
C47 C 0.65471(14) 0.74771(10) 0.41900(13) 0.0185(6) Uani 1 1 d . . . . .
C48 C 0.66498(16) 0.71328(11) 0.47436(14) 0.0240(7) Uani 1 1 d . . . . .
H48 H 0.7012 0.7134 0.5150 0.029 Uiso 1 1 calc R U . . .
C49 C 0.61241(17) 0.68292(11) 0.45372(15) 0.0265(7) Uani 1 1 d . . . . .
H49 H 0.6037 0.6565 0.4764 0.032 Uiso 1 1 calc R U . . .
C50 C 0.56887(16) 0.69898(11) 0.38630(15) 0.0247(7) Uani 1 1 d . . . . .
H50 H 0.5164 0.6873 0.3731 0.030 Uiso 1 1 calc R U . . .
C51 C 0.61987(15) 0.69101(10) 0.33328(14) 0.0190(6) Uani 1 1 d . . . . .
C52 C 0.58419(15) 0.71081(10) 0.26247(14) 0.0200(6) Uani 1 1 d . . . . .
H52 H 0.5324 0.7002 0.2426 0.024 Uiso 1 1 calc R U . . .
C53 C 0.64201(15) 0.70475(10) 0.21871(14) 0.0210(6) Uani 1 1 d . . . . .
H53 H 0.6400 0.6839 0.1835 0.025 Uiso 1 1 calc R U . . .
C54 C 0.69582(15) 0.73443(10) 0.23970(13) 0.0193(6) Uani 1 1 d . . . . .
H54 H 0.7400 0.7394 0.2228 0.023 Uiso 1 1 calc R U . . .
C55 C 0.67103(14) 0.75873(10) 0.29702(13) 0.0167(6) Uani 1 1 d . . . . .
C56 C 0.69819(16) 0.80467(10) 0.31686(14) 0.0220(6) Uani 1 1 d . . . . .
H56A H 0.7536 0.8044 0.3306 0.026 Uiso 1 1 calc R U . . .
H56B H 0.6844 0.8247 0.2780 0.026 Uiso 1 1 calc R U . . .
N57 N 0.66571(13) 0.82171(8) 0.37217(11) 0.0207(5) Uani 1 1 d . . . . .
C58 C 0.68094(16) 0.79520(10) 0.43354(13) 0.0224(7) Uani 1 1 d . . . . .
H58A H 0.6546 0.8084 0.4666 0.027 Uiso 1 1 calc R U . . .
H58B H 0.7355 0.7955 0.4528 0.027 Uiso 1 1 calc R U . . .
C59 C 0.68293(14) 0.72584(10) 0.35863(13) 0.0172(6) Uani 1 1 d . . . . .
C60 C 0.63931(16) 0.64251(10) 0.33285(14) 0.0225(7) Uani 1 1 d . . . . .
C61 C 0.61139(16) 0.85323(10) 0.35993(14) 0.0208(6) Uani 1 1 d . . . . .
C62 C 0.59046(16) 0.87605(10) 0.41832(14) 0.0217(6) Uani 1 1 d . . . . .
C63 C 0.64642(17) 0.89298(11) 0.46892(14) 0.0265(7) Uani 1 1 d . . . . .
H63 H 0.6977 0.8897 0.4664 0.032 Uiso 1 1 calc R U . . .
C64 C 0.62762(18) 0.91470(11) 0.52312(15) 0.0293(7) Uani 1 1 d . . . . .
H64 H 0.6658 0.9262 0.5578 0.035 Uiso 1 1 calc R U . . .
C65 C 0.55256(18) 0.91938(11) 0.52606(15) 0.0292(7) Uani 1 1 d . . . . .
H65 H 0.5395 0.9333 0.5637 0.035 Uiso 1 1 calc R U . . .
C66 C 0.49630(17) 0.90396(11) 0.47473(15) 0.0298(7) Uani 1 1 d . . . . .
H66 H 0.4450 0.9080 0.4767 0.036 Uiso 1 1 calc R U . . .
C67 C 0.51532(16) 0.88251(11) 0.42037(15) 0.0260(7) Uani 1 1 d . . . . .
H67 H 0.4771 0.8723 0.3847 0.031 Uiso 1 1 calc R U . . .
C68 C 0.76517(15) 0.71376(10) 0.38142(13) 0.0216(6) Uani 1 1 d . . . . .
C69 C 0.87421(15) 0.68220(12) 0.35849(15) 0.0279(7) Uani 1 1 d . . . . .
H69A H 0.8888 0.6582 0.3314 0.042 Uiso 1 1 calc R U . . .
H69B H 0.8874 0.6740 0.4058 0.042 Uiso 1 1 calc R U . . .
H69C H 0.9007 0.7095 0.3512 0.042 Uiso 1 1 calc R U . . .
O22 O 0.93290(10) 0.07677(7) 0.61245(10) 0.0230(5) Uani 1 1 d . . . . .
O23 O 0.91571(10) 0.09231(7) 0.73194(9) 0.0205(4) Uani 1 1 d . . . . .
O24 O 0.81176(12) -0.04182(8) 0.64216(11) 0.0316(5) Uani 1 1 d . . . . .
O25 O 0.91010(12) -0.04418(8) 0.72880(11) 0.0335(5) Uani 1 1 d . . . . .
H25O H 0.9006 -0.0740 0.7267 0.050 Uiso 1 1 d R U . . .
O26 O 0.92408(12) 0.20354(7) 0.69286(10) 0.0271(5) Uani 1 1 d . . . . .
O27 O 0.70207(11) 0.06404(8) 0.57565(10) 0.0303(5) Uani 1 1 d . . . . .
O28 O 0.71174(10) 0.02526(7) 0.66959(10) 0.0266(5) Uani 1 1 d . . . . .
C70 C 0.85276(15) 0.07922(11) 0.58850(14) 0.0237(7) Uani 1 1 d . . . . .
C71 C 0.84106(16) 0.04279(11) 0.53555(14) 0.0275(7) Uani 1 1 d . . . . .
H71 H 0.8050 0.0422 0.4948 0.033 Uiso 1 1 calc R U . . .
C72 C 0.89204(17) 0.01217(12) 0.55882(15) 0.0296(7) Uani 1 1 d . . . . .
H72 H 0.8996 -0.0153 0.5382 0.035 Uiso 1 1 calc R U . . .
C73 C 0.93627(17) 0.02973(11) 0.62530(15) 0.0275(7) Uani 1 1 d . . . . .
H73 H 0.9880 0.0173 0.6397 0.033 Uiso 1 1 calc R U . . .
C74 C 0.88390(16) 0.02459(10) 0.67774(14) 0.0231(7) Uani 1 1 d . . . . .
C75 C 0.91979(15) 0.04581(10) 0.74753(14) 0.0216(6) Uani 1 1 d . . . . .
H75 H 0.9709 0.0345 0.7686 0.026 Uiso 1 1 calc R U . . .
C76 C 0.86108(16) 0.04279(11) 0.79080(14) 0.0239(7) Uani 1 1 d . . . . .
H76 H 0.8615 0.0232 0.8272 0.029 Uiso 1 1 calc R U . . .
C77 C 0.80918(16) 0.07314(10) 0.76739(13) 0.0223(7) Uani 1 1 d . . . . .
H77 H 0.7651 0.0799 0.7835 0.027 Uiso 1 1 calc R U . . .
C78 C 0.83604(14) 0.09472(10) 0.70911(13) 0.0198(6) Uani 1 1 d . . . . .
C79 C 0.81187(16) 0.14080(10) 0.68597(14) 0.0234(7) Uani 1 1 d . . . . .
H79A H 0.7564 0.1417 0.6725 0.028 Uiso 1 1 calc R U . . .
H79B H 0.8272 0.1619 0.7234 0.028 Uiso 1 1 calc R U . . .
N80 N 0.84504(13) 0.15478(9) 0.62926(11) 0.0234(6) Uani 1 1 d . . . . .
C81 C 0.82912(16) 0.12637(10) 0.57001(14) 0.0240(7) Uani 1 1 d . . . . .
H81A H 0.8566 0.1376 0.5364 0.029 Uiso 1 1 calc R U . . .
H81B H 0.7747 0.1272 0.5502 0.029 Uiso 1 1 calc R U . . .
C82 C 0.82293(14) 0.06002(10) 0.64974(13) 0.0208(6) Uani 1 1 d . . . . .
C83 C 0.86249(16) -0.02325(11) 0.68067(14) 0.0240(7) Uani 1 1 d . . . . .
C84 C 0.89641(15) 0.18773(10) 0.63699(14) 0.0224(7) Uani 1 1 d . . . . .
C85 C 0.91653(16) 0.20735(10) 0.57584(14) 0.0222(6) Uani 1 1 d . . . . .
C86 C 0.86018(17) 0.22116(12) 0.52293(15) 0.0298(8) Uani 1 1 d . . . . .
H86 H 0.8090 0.2171 0.5252 0.036 Uiso 1 1 calc R U . . .
C87 C 0.87835(18) 0.24076(12) 0.46697(16) 0.0348(8) Uani 1 1 d . . . . .
H87 H 0.8397 0.2503 0.4311 0.042 Uiso 1 1 calc R U . . .
C88 C 0.95304(18) 0.24642(12) 0.46362(16) 0.0329(8) Uani 1 1 d . . . . .
H88 H 0.9658 0.2588 0.4248 0.039 Uiso 1 1 calc R U . . .
C89 C 1.00924(17) 0.23394(12) 0.51715(16) 0.0314(8) Uani 1 1 d . . . . .
H89 H 1.0604 0.2387 0.5153 0.038 Uiso 1 1 calc R U . . .
C90 C 0.99136(16) 0.21453(11) 0.57327(15) 0.0275(7) Uani 1 1 d . . . . .
H90 H 1.0301 0.2062 0.6098 0.033 Uiso 1 1 calc R U . . .
C91 C 0.74000(15) 0.04910(10) 0.62718(14) 0.0227(7) Uani 1 1 d . . . . .
C92 C 0.63191(15) 0.01643(12) 0.64976(15) 0.0277(7) Uani 1 1 d . . . . .
H92A H 0.6183 -0.0080 0.6767 0.042 Uiso 1 1 calc R U . . .
H92B H 0.6197 0.0082 0.6025 0.042 Uiso 1 1 calc R U . . .
H92C H 0.6037 0.0431 0.6567 0.042 Uiso 1 1 calc R U . . .
O29 O 0.92294(10) 0.41805(7) 0.61742(10) 0.0226(5) Uani 1 1 d . . . . .
O30 O 0.89598(10) 0.42877(7) 0.73511(9) 0.0211(4) Uani 1 1 d . . . . .
O31 O 0.84125(13) 0.29224(8) 0.71656(14) 0.0442(6) Uani 1 1 d . . . . .
O32 O 0.95073(11) 0.28904(8) 0.68414(11) 0.0314(5) Uani 1 1 d . . . . .
H32O H 0.9339 0.2564 0.6940 0.047 Uiso 1 1 d R U . . .
O33 O 0.87513(14) 0.53096(8) 0.69911(10) 0.0355(6) Uani 1 1 d . . . . .
O34 O 0.74588(13) 0.32604(9) 0.59315(13) 0.0455(7) Uani 1 1 d . . . . .
O35 O 0.69050(11) 0.37500(7) 0.64867(10) 0.0275(5) Uani 1 1 d . . . . .
C93 C 0.84519(15) 0.40902(10) 0.59119(14) 0.0214(6) Uani 1 1 d . . . . .
C94 C 0.85113(17) 0.37318(11) 0.54032(15) 0.0276(7) Uani 1 1 d . . . . .
H94 H 0.8179 0.3680 0.4987 0.033 Uiso 1 1 calc R U . . .
C95 C 0.91331(17) 0.35043(11) 0.56686(15) 0.0295(7) Uani 1 1 d . . . . .
H95 H 0.9334 0.3255 0.5480 0.035 Uiso 1 1 calc R U . . .
C96 C 0.94529(16) 0.37268(10) 0.63335(15) 0.0244(7) Uani 1 1 d . . . . .
H96 H 1.0003 0.3682 0.6503 0.029 Uiso 1 1 calc R U . . .
C97 C 0.89434(15) 0.35963(10) 0.68342(14) 0.0216(6) Uani 1 1 d . . . . .
C98 C 0.91692(16) 0.38374(10) 0.75313(14) 0.0228(7) Uani 1 1 d . . . . .
H98 H 0.9704 0.3796 0.7766 0.027 Uiso 1 1 calc R U . . .
C99 C 0.85867(16) 0.37220(11) 0.79442(14) 0.0239(7) Uani 1 1 d . . . . .
H99 H 0.8649 0.3525 0.8314 0.029 Uiso 1 1 calc R U . . .
C100 C 0.79740(16) 0.39526(10) 0.76836(14) 0.0214(6) Uani 1 1 d . . . . .
H100 H 0.7512 0.3960 0.7831 0.026 Uiso 1 1 calc R U . . .
C101 C 0.81730(15) 0.42027(10) 0.70982(14) 0.0196(6) Uani 1 1 d . . . . .
C102 C 0.77685(16) 0.46255(10) 0.68473(14) 0.0230(7) Uani 1 1 d . . . . .
H10C H 0.7226 0.4564 0.6694 0.028 Uiso 1 1 calc R U . . .
H10D H 0.7828 0.4845 0.7214 0.028 Uiso 1 1 calc R U . . .
N103 N 0.80738(13) 0.48089(9) 0.62927(11) 0.0228(6) Uani 1 1 d . . . . .
C104 C 0.80273(16) 0.45187(10) 0.57147(14) 0.0241(7) Uani 1 1 d . . . . .
H10E H 0.8242 0.4672 0.5369 0.029 Uiso 1 1 calc R U . . .
H10F H 0.7494 0.4451 0.5523 0.029 Uiso 1 1 calc R U . . .
C105 C 0.82071(15) 0.38541(10) 0.65295(14) 0.0201(6) Uani 1 1 d . . . . .
C106 C 0.89069(16) 0.31012(11) 0.69531(16) 0.0284(7) Uani 1 1 d . . . . .
C107 C 0.85647(17) 0.51510(11) 0.64216(14) 0.0256(7) Uani 1 1 d . . . . .
C108 C 0.88296(17) 0.53638(11) 0.58493(14) 0.0263(7) Uani 1 1 d . . . . .
C109 C 0.83422(18) 0.56293(12) 0.54089(15) 0.0328(8) Uani 1 1 d . . . . .
H109 H 0.7840 0.5667 0.5465 0.039 Uiso 1 1 calc R U . . .
C110 C 0.8579(2) 0.58406(13) 0.48856(16) 0.0376(8) Uani 1 1 d . . . . .
H110 H 0.8238 0.6019 0.4581 0.045 Uiso 1 1 calc R U . . .
C111 C 0.9309(2) 0.57912(12) 0.48094(16) 0.0356(8) Uani 1 1 d . . . . .
H111 H 0.9473 0.5932 0.4450 0.043 Uiso 1 1 calc R U . . .
C112 C 0.9797(2) 0.55376(14) 0.52560(19) 0.0487(10) Uani 1 1 d . . . . .
H112 H 1.0303 0.5508 0.5208 0.058 Uiso 1 1 calc R U . . .
C113 C 0.9563(2) 0.53217(14) 0.57805(19) 0.0474(10) Uani 1 1 d . . . . .
H113 H 0.9907 0.5147 0.6088 0.057 Uiso 1 1 calc R U . . .
C114 C 0.75017(16) 0.35840(12) 0.62918(15) 0.0276(7) Uani 1 1 d . . . . .
C115 C 0.62052(15) 0.35146(11) 0.62586(15) 0.0272(7) Uani 1 1 d . . . . .
H11A H 0.6064 0.3531 0.5771 0.041 Uiso 1 1 calc R U . . .
H11B H 0.5811 0.3650 0.6454 0.041 Uiso 1 1 calc R U . . .
H11C H 0.6268 0.3203 0.6396 0.041 Uiso 1 1 calc R U . . .
O36 O 0.94600(10) 0.74115(7) 0.65993(9) 0.0195(4) Uani 1 1 d . . . . .
O37 O 0.91312(10) 0.75813(7) 0.77353(9) 0.0190(4) Uani 1 1 d . . . . .
O38 O 0.85593(12) 0.62427(7) 0.77744(11) 0.0285(5) Uani 1 1 d . . . . .
O39 O 0.92970(11) 0.61126(7) 0.70537(10) 0.0240(5) Uani 1 1 d . . . . .
H39O H 0.9199 0.5820 0.7109 0.036 Uiso 1 1 d R U . . .
O40 O 0.89254(11) 0.86916(7) 0.72018(10) 0.0257(5) Uani 1 1 d . . . . .
O41 O 0.75703(12) 0.65352(8) 0.64750(12) 0.0348(6) Uani 1 1 d . . . . .
O42 O 0.70474(11) 0.71814(8) 0.66695(11) 0.0302(5) Uani 1 1 d . . . . .
C116 C 0.86843(14) 0.73526(10) 0.63006(13) 0.0185(6) Uani 1 1 d . . . . .
C117 C 0.87243(15) 0.69739(10) 0.58184(13) 0.0197(6) Uani 1 1 d . . . . .
H117 H 0.8405 0.6925 0.5395 0.024 Uiso 1 1 calc R U . . .
C118 C 0.93011(15) 0.67264(10) 0.61156(13) 0.0201(6) Uani 1 1 d . . . . .
H118 H 0.9481 0.6463 0.5947 0.024 Uiso 1 1 calc R U . . .
C119 C 0.96161(15) 0.69505(10) 0.67836(14) 0.0196(6) Uani 1 1 d . . . . .
H119 H 1.0154 0.6882 0.6979 0.024 Uiso 1 1 calc R U . . .
C120 C 0.90539(14) 0.68673(10) 0.72627(13) 0.0175(6) Uani 1 1 d . . . . .
C121 C 0.92569(15) 0.71256(10) 0.79476(13) 0.0191(6) Uani 1 1 d . . . . .
H121 H 0.9769 0.7063 0.8218 0.023 Uiso 1 1 calc R U . . .
C122 C 0.86177(15) 0.70617(10) 0.83185(13) 0.0201(6) Uani 1 1 d . . . . .
H122 H 0.8621 0.6876 0.8694 0.024 Uiso 1 1 calc R U . . .
C123 C 0.80566(15) 0.73172(10) 0.80116(13) 0.0195(6) Uani 1 1 d . . . . .
H123 H 0.7580 0.7357 0.8125 0.023 Uiso 1 1 calc R U . . .
C124 C 0.83456(14) 0.75313(10) 0.74386(13) 0.0190(6) Uani 1 1 d . . . . .
C125 C 0.80196(16) 0.79637(10) 0.71466(14) 0.0214(6) Uani 1 1 d . . . . .
H12C H 0.7472 0.7929 0.6980 0.026 Uiso 1 1 calc R U . . .
H12D H 0.8098 0.8194 0.7499 0.026 Uiso 1 1 calc R U . . .
N126 N 0.83705(13) 0.81077(8) 0.65953(11) 0.0204(5) Uani 1 1 d . . . . .
C127 C 0.83327(16) 0.77897(10) 0.60469(13) 0.0211(6) Uani 1 1 d . . . . .
H12E H 0.8599 0.7913 0.5712 0.025 Uiso 1 1 calc R U . . .
H12F H 0.7802 0.7741 0.5827 0.025 Uiso 1 1 calc R U . . .
C128 C 0.83703(14) 0.71533(10) 0.69083(13) 0.0166(6) Uani 1 1 d . . . . .
C129 C 0.89268(15) 0.63797(10) 0.73846(13) 0.0185(6) Uani 1 1 d . . . . .
C130 C 0.87971(15) 0.84773(10) 0.66658(14) 0.0211(6) Uani 1 1 d . . . . .
C131 C 0.90749(16) 0.86474(10) 0.60744(14) 0.0227(7) Uani 1 1 d . . . . .
C132 C 0.85696(17) 0.87711(11) 0.54996(14) 0.0276(7) Uani 1 1 d . . . . .
H132 H 0.8046 0.8738 0.5476 0.033 Uiso 1 1 calc R U . . .
C133 C 0.8824(2) 0.89429(12) 0.49608(15) 0.0335(8) Uani 1 1 d . . . . .
H133 H 0.8476 0.9030 0.4570 0.040 Uiso 1 1 calc R U . . .
C134 C 0.9584(2) 0.89881(12) 0.49910(17) 0.0375(9) Uani 1 1 d . . . . .
H134 H 0.9760 0.9096 0.4615 0.045 Uiso 1 1 calc R U . . .
C135 C 1.0093(2) 0.88758(13) 0.55726(19) 0.0428(9) Uani 1 1 d . . . . .
H135 H 1.0616 0.8911 0.5594 0.051 Uiso 1 1 calc R U . . .
C136 C 0.98417(17) 0.87126(12) 0.61210(17) 0.0333(8) Uani 1 1 d . . . . .
H136 H 1.0188 0.8646 0.6523 0.040 Uiso 1 1 calc R U . . .
C137 C 0.76349(15) 0.69120(11) 0.66662(14) 0.0216(7) Uani 1 1 d . . . . .
C138 C 0.63031(16) 0.69959(13) 0.64632(16) 0.0358(9) Uani 1 1 d . . . . .
H13A H 0.5966 0.7132 0.6722 0.054 Uiso 1 1 calc R U . . .
H13B H 0.6323 0.6675 0.6540 0.054 Uiso 1 1 calc R U . . .
H13C H 0.6116 0.7055 0.5988 0.054 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.439(3) . ?
O1 C4 1.450(4) . ?
O2 C6 1.445(4) . ?
O2 C9 1.448(3) . ?
O3 C14 1.202(4) . ?
O4 C14 1.327(3) . ?
O4 H4O 0.9094 . ?
O5 C15 1.240(4) . ?
O6 C22 1.207(4) . ?
O7 C22 1.350(3) . ?
O7 C23 1.450(3) . ?
C1 C12 1.511(4) . ?
C1 C2 1.520(4) . ?
C1 C13 1.595(4) . ?
C2 C3 1.329(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.520(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.569(4) . ?
C4 H4 1.0000 . ?
C5 C14 1.510(4) . ?
C5 C13 1.561(4) . ?
C5 C6 1.574(4) . ?
C6 C7 1.525(4) . ?
C6 H6 1.0000 . ?
C7 C8 1.327(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.526(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.503(4) . ?
C9 C13 1.580(4) . ?
C10 N11 1.471(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N11 C15 1.350(4) . ?
N11 C12 1.461(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C22 1.516(4) . ?
C15 C16 1.495(4) . ?
C16 C21 1.372(4) . ?
C16 C17 1.380(4) . ?
C17 C18 1.387(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.375(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.375(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.392(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O8 C24 1.431(3) . ?
O8 C27 1.454(4) . ?
O9 C32 1.442(3) . ?
O9 C29 1.448(4) . ?
O10 C37 1.211(3) . ?
O11 C37 1.313(4) . ?
O11 H11O 0.9097 . ?
O12 C38 1.248(4) . ?
O13 C45 1.205(4) . ?
O14 C45 1.322(4) . ?
O14 C46 1.450(3) . ?
C24 C35 1.513(4) . ?
C24 C25 1.525(4) . ?
C24 C36 1.583(4) . ?
C25 C26 1.329(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.522(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.574(4) . ?
C27 H27 1.0000 . ?
C28 C37 1.527(4) . ?
C28 C36 1.568(4) . ?
C28 C29 1.574(4) . ?
C29 C30 1.527(4) . ?
C29 H29 1.0000 . ?
C30 C31 1.334(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.523(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.499(4) . ?
C32 C36 1.578(4) . ?
C33 N34 1.473(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
N34 C38 1.354(4) . ?
N34 C35 1.463(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C45 1.515(4) . ?
C38 C39 1.499(4) . ?
C39 C44 1.384(4) . ?
C39 C40 1.394(4) . ?
C40 C41 1.383(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.390(5) . ?
C41 H41 0.9500 . ?
C42 C43 1.389(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.390(5) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
O15 C47 1.438(3) . ?
O15 C50 1.445(4) . ?
O16 C55 1.432(3) . ?
O16 C52 1.434(4) . ?
O17 C60 1.222(4) . ?
O18 C60 1.330(4) . ?
O18 H18O 0.9138 . ?
O19 C61 1.249(3) . ?
O20 C68 1.224(3) . ?
O21 C68 1.316(3) . ?
O21 C69 1.452(3) . ?
C47 C58 1.517(4) . ?
C47 C48 1.519(4) . ?
C47 C59 1.577(4) . ?
C48 C49 1.328(4) . ?
C48 H48 0.9500 . ?
C49 C50 1.523(4) . ?
C49 H49 0.9500 . ?
C50 C51 1.585(4) . ?
C50 H50 1.0000 . ?
C51 C60 1.503(4) . ?
C51 C59 1.562(4) . ?
C51 C52 1.579(4) . ?
C52 C53 1.526(4) . ?
C52 H52 1.0000 . ?
C53 C54 1.330(4) . ?
C53 H53 0.9500 . ?
C54 C55 1.528(4) . ?
C54 H54 0.9500 . ?
C55 C56 1.497(4) . ?
C55 C59 1.583(4) . ?
C56 N57 1.473(3) . ?
C56 H56A 0.9900 . ?
C56 H56B 0.9900 . ?
N57 C61 1.356(4) . ?
N57 C58 1.467(4) . ?
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
C59 C68 1.517(4) . ?
C61 C62 1.495(4) . ?
C62 C67 1.390(4) . ?
C62 C63 1.392(4) . ?
C63 C64 1.390(4) . ?
C63 H63 0.9500 . ?
C64 C65 1.387(4) . ?
C64 H64 0.9500 . ?
C65 C66 1.388(4) . ?
C65 H65 0.9500 . ?
C66 C67 1.391(4) . ?
C66 H66 0.9500 . ?
C67 H67 0.9500 . ?
C69 H69A 0.9800 . ?
C69 H69B 0.9800 . ?
C69 H69C 0.9800 . ?
O22 C73 1.440(4) . ?
O22 C70 1.442(3) . ?
O23 C78 1.431(3) . ?
O23 C75 1.434(4) . ?
O24 C83 1.220(4) . ?
O25 C83 1.330(4) . ?
O25 H25O 0.9138 . ?
O26 C84 1.246(3) . ?
O27 C91 1.222(3) . ?
O28 C91 1.311(4) . ?
O28 C92 1.450(3) . ?
C70 C81 1.509(5) . ?
C70 C71 1.526(4) . ?
C70 C82 1.575(4) . ?
C71 C72 1.325(5) . ?
C71 H71 0.9500 . ?
C72 C73 1.527(4) . ?
C72 H72 0.9500 . ?
C73 C74 1.583(4) . ?
C73 H73 1.0000 . ?
C74 C83 1.497(4) . ?
C74 C82 1.561(4) . ?
C74 C75 1.579(4) . ?
C75 C76 1.524(4) . ?
C75 H75 1.0000 . ?
C76 C77 1.331(4) . ?
C76 H76 0.9500 . ?
C77 C78 1.525(4) . ?
C77 H77 0.9500 . ?
C78 C79 1.502(4) . ?
C78 C82 1.584(4) . ?
C79 N80 1.476(4) . ?
C79 H79A 0.9900 . ?
C79 H79B 0.9900 . ?
N80 C84 1.350(4) . ?
N80 C81 1.464(4) . ?
C81 H81A 0.9900 . ?
C81 H81B 0.9900 . ?
C82 C91 1.520(4) . ?
C84 C85 1.497(4) . ?
C85 C90 1.390(4) . ?
C85 C86 1.394(4) . ?
C86 C87 1.388(4) . ?
C86 H86 0.9500 . ?
C87 C88 1.385(4) . ?
C87 H87 0.9500 . ?
C88 C89 1.389(5) . ?
C88 H88 0.9500 . ?
C89 C90 1.386(4) . ?
C89 H89 0.9500 . ?
C90 H90 0.9500 . ?
C92 H92A 0.9800 . ?
C92 H92B 0.9800 . ?
C92 H92C 0.9800 . ?
O29 C93 1.432(3) . ?
O29 C96 1.443(4) . ?
O30 C98 1.436(4) . ?
O30 C101 1.442(3) . ?
O31 C106 1.204(4) . ?
O32 C106 1.323(4) . ?
O32 H32O 1.0621 . ?
O33 C107 1.242(4) . ?
O34 C114 1.215(4) . ?
O35 C114 1.329(4) . ?
O35 C115 1.448(3) . ?
C93 C104 1.515(4) . ?
C93 C94 1.519(4) . ?
C93 C105 1.592(4) . ?
C94 C95 1.339(5) . ?
C94 H94 0.9500 . ?
C95 C96 1.522(4) . ?
C95 H95 0.9500 . ?
C96 C97 1.567(4) . ?
C96 H96 1.0000 . ?
C97 C106 1.514(5) . ?
C97 C105 1.563(4) . ?
C97 C98 1.579(4) . ?
C98 C99 1.525(4) . ?
C98 H98 1.0000 . ?
C99 C100 1.329(4) . ?
C99 H99 0.9500 . ?
C100 C101 1.521(4) . ?
C100 H100 0.9500 . ?
C101 C102 1.507(4) . ?
C101 C105 1.579(4) . ?
C102 N103 1.471(4) . ?
C102 H10C 0.9900 . ?
C102 H10D 0.9900 . ?
N103 C107 1.353(4) . ?
N103 C104 1.460(4) . ?
C104 H10E 0.9900 . ?
C104 H10F 0.9900 . ?
C105 C114 1.513(4) . ?
C107 C108 1.500(4) . ?
C108 C113 1.377(5) . ?
C108 C109 1.382(4) . ?
C109 C110 1.389(5) . ?
C109 H109 0.9500 . ?
C110 C111 1.377(5) . ?
C110 H110 0.9500 . ?
C111 C112 1.369(5) . ?
C111 H111 0.9500 . ?
C112 C113 1.394(5) . ?
C112 H112 0.9500 . ?
C113 H113 0.9500 . ?
C115 H11A 0.9800 . ?
C115 H11B 0.9800 . ?
C115 H11C 0.9800 . ?
O36 C116 1.429(3) . ?
O36 C119 1.451(4) . ?
O37 C124 1.442(3) . ?
O37 C121 1.443(4) . ?
O38 C129 1.214(3) . ?
O39 C129 1.322(3) . ?
O39 H39O 0.9107 . ?
O40 C130 1.253(4) . ?
O41 C137 1.198(4) . ?
O42 C137 1.343(4) . ?
O42 C138 1.446(3) . ?
C116 C127 1.508(4) . ?
C116 C117 1.520(4) . ?
C116 C128 1.590(4) . ?
C117 C118 1.328(4) . ?
C117 H117 0.9500 . ?
C118 C119 1.528(4) . ?
C118 H118 0.9500 . ?
C119 C120 1.576(4) . ?
C119 H119 1.0000 . ?
C120 C129 1.515(4) . ?
C120 C128 1.564(4) . ?
C120 C121 1.580(4) . ?
C121 C122 1.526(4) . ?
C121 H121 1.0000 . ?
C122 C123 1.329(4) . ?
C122 H122 0.9500 . ?
C123 C124 1.524(4) . ?
C123 H123 0.9500 . ?
C124 C125 1.503(4) . ?
C124 C128 1.580(4) . ?
C125 N126 1.472(3) . ?
C125 H12C 0.9900 . ?
C125 H12D 0.9900 . ?
N126 C130 1.347(4) . ?
N126 C127 1.467(4) . ?
C127 H12E 0.9900 . ?
C127 H12F 0.9900 . ?
C128 C137 1.514(4) . ?
C130 C131 1.495(4) . ?
C131 C132 1.387(4) . ?
C131 C136 1.393(4) . ?
C132 C133 1.382(4) . ?
C132 H132 0.9500 . ?
C133 C134 1.377(5) . ?
C133 H133 0.9500 . ?
C134 C135 1.392(5) . ?
C134 H134 0.9500 . ?
C135 C136 1.387(5) . ?
C135 H135 0.9500 . ?
C136 H136 0.9500 . ?
C138 H13A 0.9800 . ?
C138 H13B 0.9800 . ?
C138 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C4 96.4(2) . . ?
C6 O2 C9 96.6(2) . . ?
C14 O4 H4O 107.2 . . ?
C22 O7 C23 116.3(2) . . ?
O1 C1 C12 110.2(2) . . ?
O1 C1 C2 100.9(2) . . ?
C12 C1 C2 121.9(2) . . ?
O1 C1 C13 100.9(2) . . ?
C12 C1 C13 113.1(2) . . ?
C2 C1 C13 107.1(2) . . ?
C3 C2 C1 105.4(3) . . ?
C3 C2 H2 127.3 . . ?
C1 C2 H2 127.3 . . ?
C2 C3 C4 106.0(3) . . ?
C2 C3 H3 127.0 . . ?
C4 C3 H3 127.0 . . ?
O1 C4 C3 100.3(2) . . ?
O1 C4 C5 102.1(2) . . ?
C3 C4 C5 107.7(2) . . ?
O1 C4 H4 115.0 . . ?
C3 C4 H4 115.0 . . ?
C5 C4 H4 115.0 . . ?
C14 C5 C13 118.8(2) . . ?
C14 C5 C4 113.3(2) . . ?
C13 C5 C4 100.5(2) . . ?
C14 C5 C6 109.9(2) . . ?
C13 C5 C6 99.9(2) . . ?
C4 C5 C6 113.7(2) . . ?
O2 C6 C7 100.2(2) . . ?
O2 C6 C5 101.4(2) . . ?
C7 C6 C5 108.5(2) . . ?
O2 C6 H6 115.0 . . ?
C7 C6 H6 115.0 . . ?
C5 C6 H6 115.0 . . ?
C8 C7 C6 106.5(3) . . ?
C8 C7 H7 126.8 . . ?
C6 C7 H7 126.8 . . ?
C7 C8 C9 105.2(2) . . ?
C7 C8 H8 127.4 . . ?
C9 C8 H8 127.4 . . ?
O2 C9 C10 110.8(2) . . ?
O2 C9 C8 100.4(2) . . ?
C10 C9 C8 120.8(2) . . ?
O2 C9 C13 101.2(2) . . ?
C10 C9 C13 114.4(2) . . ?
C8 C9 C13 106.7(2) . . ?
N11 C10 C9 110.8(2) . . ?
N11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
N11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C15 N11 C12 123.1(2) . . ?
C15 N11 C10 119.1(2) . . ?
C12 N11 C10 115.5(2) . . ?
N11 C12 C1 110.5(2) . . ?
N11 C12 H12A 109.5 . . ?
C1 C12 H12A 109.5 . . ?
N11 C12 H12B 109.5 . . ?
C1 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C22 C13 C5 117.8(3) . . ?
C22 C13 C9 115.5(2) . . ?
C5 C13 C9 102.0(2) . . ?
C22 C13 C1 109.5(2) . . ?
C5 C13 C1 101.1(2) . . ?
C9 C13 C1 109.8(2) . . ?
O3 C14 O4 123.2(3) . . ?
O3 C14 C5 124.7(3) . . ?
O4 C14 C5 112.0(2) . . ?
O5 C15 N11 121.1(3) . . ?
O5 C15 C16 119.6(3) . . ?
N11 C15 C16 119.1(3) . . ?
C21 C16 C17 119.9(3) . . ?
C21 C16 C15 121.5(3) . . ?
C17 C16 C15 118.4(3) . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 119.9(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 119.7(3) . . ?
C16 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
O6 C22 O7 122.8(3) . . ?
O6 C22 C13 125.4(3) . . ?
O7 C22 C13 111.7(3) . . ?
O7 C23 H23A 109.5 . . ?
O7 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O7 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C24 O8 C27 96.3(2) . . ?
C32 O9 C29 96.6(2) . . ?
C37 O11 H11O 106.2 . . ?
C45 O14 C46 117.5(3) . . ?
O8 C24 C35 109.8(2) . . ?
O8 C24 C25 101.2(2) . . ?
C35 C24 C25 120.4(2) . . ?
O8 C24 C36 101.6(2) . . ?
C35 C24 C36 114.2(2) . . ?
C25 C24 C36 107.4(2) . . ?
C26 C25 C24 104.6(3) . . ?
C26 C25 H25 127.7 . . ?
C24 C25 H25 127.7 . . ?
C25 C26 C27 106.7(3) . . ?
C25 C26 H26 126.7 . . ?
C27 C26 H26 126.7 . . ?
O8 C27 C26 99.8(2) . . ?
O8 C27 C28 101.8(2) . . ?
C26 C27 C28 108.4(2) . . ?
O8 C27 H27 115.0 . . ?
C26 C27 H27 115.0 . . ?
C28 C27 H27 115.0 . . ?
C37 C28 C36 119.5(2) . . ?
C37 C28 C29 109.4(2) . . ?
C36 C28 C29 99.2(2) . . ?
C37 C28 C27 113.4(2) . . ?
C36 C28 C27 99.9(2) . . ?
C29 C28 C27 114.8(2) . . ?
O9 C29 C30 100.1(2) . . ?
O9 C29 C28 101.8(2) . . ?
C30 C29 C28 108.6(2) . . ?
O9 C29 H29 114.8 . . ?
C30 C29 H29 114.8 . . ?
C28 C29 H29 114.8 . . ?
C31 C30 C29 106.3(2) . . ?
C31 C30 H30 126.9 . . ?
C29 C30 H30 126.9 . . ?
C30 C31 C32 105.1(2) . . ?
C30 C31 H31 127.5 . . ?
C32 C31 H31 127.5 . . ?
O9 C32 C33 110.8(2) . . ?
O9 C32 C31 100.7(2) . . ?
C33 C32 C31 120.1(2) . . ?
O9 C32 C36 101.2(2) . . ?
C33 C32 C36 115.1(2) . . ?
C31 C32 C36 106.5(2) . . ?
N34 C33 C32 111.0(2) . . ?
N34 C33 H33A 109.4 . . ?
C32 C33 H33A 109.4 . . ?
N34 C33 H33B 109.4 . . ?
C32 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
C38 N34 C35 124.4(2) . . ?
C38 N34 C33 119.3(2) . . ?
C35 N34 C33 115.3(2) . . ?
N34 C35 C24 111.0(2) . . ?
N34 C35 H35A 109.4 . . ?
C24 C35 H35A 109.4 . . ?
N34 C35 H35B 109.4 . . ?
C24 C35 H35B 109.4 . . ?
H35A C35 H35B 108.0 . . ?
C45 C36 C28 116.4(3) . . ?
C45 C36 C32 114.6(2) . . ?
C28 C36 C32 102.3(2) . . ?
C45 C36 C24 111.9(2) . . ?
C28 C36 C24 101.3(2) . . ?
C32 C36 C24 109.1(2) . . ?
O10 C37 O11 122.7(3) . . ?
O10 C37 C28 123.6(3) . . ?
O11 C37 C28 113.5(2) . . ?
O12 C38 N34 121.0(3) . . ?
O12 C38 C39 119.6(3) . . ?
N34 C38 C39 119.3(3) . . ?
C44 C39 C40 120.1(3) . . ?
C44 C39 C38 118.8(3) . . ?
C40 C39 C38 120.9(3) . . ?
C41 C40 C39 120.2(3) . . ?
C41 C40 H40 119.9 . . ?
C39 C40 H40 119.9 . . ?
C40 C41 C42 120.0(3) . . ?
C40 C41 H41 120.0 . . ?
C42 C41 H41 120.0 . . ?
C43 C42 C41 119.6(3) . . ?
C43 C42 H42 120.2 . . ?
C41 C42 H42 120.2 . . ?
C42 C43 C44 120.6(3) . . ?
C42 C43 H43 119.7 . . ?
C44 C43 H43 119.7 . . ?
C39 C44 C43 119.5(3) . . ?
C39 C44 H44 120.3 . . ?
C43 C44 H44 120.3 . . ?
O13 C45 O14 123.0(3) . . ?
O13 C45 C36 125.1(3) . . ?
O14 C45 C36 111.8(3) . . ?
O14 C46 H46A 109.5 . . ?
O14 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
O14 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C47 O15 C50 96.3(2) . . ?
C55 O16 C52 97.18(19) . . ?
C60 O18 H18O 107.3 . . ?
C68 O21 C69 114.8(2) . . ?
O15 C47 C58 110.2(2) . . ?
O15 C47 C48 101.0(2) . . ?
C58 C47 C48 120.7(2) . . ?
O15 C47 C59 101.6(2) . . ?
C58 C47 C59 114.1(2) . . ?
C48 C47 C59 106.9(2) . . ?
C49 C48 C47 105.2(3) . . ?
C49 C48 H48 127.4 . . ?
C47 C48 H48 127.4 . . ?
C48 C49 C50 106.1(3) . . ?
C48 C49 H49 127.0 . . ?
C50 C49 H49 127.0 . . ?
O15 C50 C49 100.5(2) . . ?
O15 C50 C51 101.9(2) . . ?
C49 C50 C51 107.7(2) . . ?
O15 C50 H50 115.0 . . ?
C49 C50 H50 115.0 . . ?
C51 C50 H50 115.0 . . ?
C60 C51 C59 119.8(2) . . ?
C60 C51 C52 114.5(2) . . ?
C59 C51 C52 100.8(2) . . ?
C60 C51 C50 108.8(2) . . ?
C59 C51 C50 99.4(2) . . ?
C52 C51 C50 112.6(2) . . ?
O16 C52 C53 100.3(2) . . ?
O16 C52 C51 101.5(2) . . ?
C53 C52 C51 106.9(2) . . ?
O16 C52 H52 115.4 . . ?
C53 C52 H52 115.4 . . ?
C51 C52 H52 115.4 . . ?
C54 C53 C52 106.3(2) . . ?
C54 C53 H53 126.9 . . ?
C52 C53 H53 126.9 . . ?
C53 C54 C55 104.8(2) . . ?
C53 C54 H54 127.6 . . ?
C55 C54 H54 127.6 . . ?
O16 C55 C56 111.3(2) . . ?
O16 C55 C54 101.0(2) . . ?
C56 C55 C54 121.2(2) . . ?
O16 C55 C59 101.4(2) . . ?
C56 C55 C59 112.2(2) . . ?
C54 C55 C59 107.4(2) . . ?
N57 C56 C55 111.6(2) . . ?
N57 C56 H56A 109.3 . . ?
C55 C56 H56A 109.3 . . ?
N57 C56 H56B 109.3 . . ?
C55 C56 H56B 109.3 . . ?
H56A C56 H56B 108.0 . . ?
C61 N57 C58 122.8(2) . . ?
C61 N57 C56 119.6(2) . . ?
C58 N57 C56 115.7(2) . . ?
N57 C58 C47 110.4(2) . . ?
N57 C58 H58A 109.6 . . ?
C47 C58 H58A 109.6 . . ?
N57 C58 H58B 109.6 . . ?
C47 C58 H58B 109.6 . . ?
H58A C58 H58B 108.1 . . ?
C68 C59 C51 123.5(2) . . ?
C68 C59 C47 108.6(2) . . ?
C51 C59 C47 101.9(2) . . ?
C68 C59 C55 111.1(2) . . ?
C51 C59 C55 100.6(2) . . ?
C47 C59 C55 110.5(2) . . ?
O17 C60 O18 123.3(3) . . ?
O17 C60 C51 125.7(3) . . ?
O18 C60 C51 110.9(2) . . ?
O19 C61 N57 121.4(3) . . ?
O19 C61 C62 120.4(3) . . ?
N57 C61 C62 118.0(2) . . ?
C67 C62 C63 120.0(3) . . ?
C67 C62 C61 120.1(3) . . ?
C63 C62 C61 119.8(3) . . ?
C64 C63 C62 120.3(3) . . ?
C64 C63 H63 119.9 . . ?
C62 C63 H63 119.9 . . ?
C65 C64 C63 119.3(3) . . ?
C65 C64 H64 120.4 . . ?
C63 C64 H64 120.4 . . ?
C64 C65 C66 120.9(3) . . ?
C64 C65 H65 119.6 . . ?
C66 C65 H65 119.6 . . ?
C65 C66 C67 119.7(3) . . ?
C65 C66 H66 120.1 . . ?
C67 C66 H66 120.1 . . ?
C62 C67 C66 119.8(3) . . ?
C62 C67 H67 120.1 . . ?
C66 C67 H67 120.1 . . ?
O20 C68 O21 122.6(3) . . ?
O20 C68 C59 121.7(3) . . ?
O21 C68 C59 115.4(2) . . ?
O21 C69 H69A 109.5 . . ?
O21 C69 H69B 109.5 . . ?
H69A C69 H69B 109.5 . . ?
O21 C69 H69C 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
C73 O22 C70 96.6(2) . . ?
C78 O23 C75 97.2(2) . . ?
C83 O25 H25O 110.0 . . ?
C91 O28 C92 114.9(2) . . ?
O22 C70 C81 110.5(2) . . ?
O22 C70 C71 100.9(2) . . ?
C81 C70 C71 120.5(2) . . ?
O22 C70 C82 101.5(2) . . ?
C81 C70 C82 114.7(2) . . ?
C71 C70 C82 106.3(2) . . ?
C72 C71 C70 105.0(3) . . ?
C72 C71 H71 127.5 . . ?
C70 C71 H71 127.5 . . ?
C71 C72 C73 106.4(3) . . ?
C71 C72 H72 126.8 . . ?
C73 C72 H72 126.8 . . ?
O22 C73 C72 100.5(2) . . ?
O22 C73 C74 102.2(2) . . ?
C72 C73 C74 106.9(2) . . ?
O22 C73 H73 115.2 . . ?
C72 C73 H73 115.2 . . ?
C74 C73 H73 115.2 . . ?
C83 C74 C82 120.1(2) . . ?
C83 C74 C75 114.6(2) . . ?
C82 C74 C75 100.8(2) . . ?
C83 C74 C73 108.6(2) . . ?
C82 C74 C73 99.5(2) . . ?
C75 C74 C73 112.3(2) . . ?
O23 C75 C76 100.2(2) . . ?
O23 C75 C74 101.6(2) . . ?
C76 C75 C74 107.0(2) . . ?
O23 C75 H75 115.4 . . ?
C76 C75 H75 115.4 . . ?
C74 C75 H75 115.4 . . ?
C77 C76 C75 106.2(3) . . ?
C77 C76 H76 126.9 . . ?
C75 C76 H76 126.9 . . ?
C76 C77 C78 104.9(2) . . ?
C76 C77 H77 127.6 . . ?
C78 C77 H77 127.6 . . ?
O23 C78 C79 111.2(2) . . ?
O23 C78 C77 100.9(2) . . ?
C79 C78 C77 121.3(2) . . ?
O23 C78 C82 101.6(2) . . ?
C79 C78 C82 112.3(2) . . ?
C77 C78 C82 107.3(2) . . ?
N80 C79 C78 111.8(2) . . ?
N80 C79 H79A 109.3 . . ?
C78 C79 H79A 109.3 . . ?
N80 C79 H79B 109.3 . . ?
C78 C79 H79B 109.3 . . ?
H79A C79 H79B 107.9 . . ?
C84 N80 C81 122.8(2) . . ?
C84 N80 C79 120.2(2) . . ?
C81 N80 C79 116.2(2) . . ?
N80 C81 C70 110.1(2) . . ?
N80 C81 H81A 109.6 . . ?
C70 C81 H81A 109.6 . . ?
N80 C81 H81B 109.6 . . ?
C70 C81 H81B 109.6 . . ?
H81A C81 H81B 108.1 . . ?
C91 C82 C74 123.4(3) . . ?
C91 C82 C70 108.7(2) . . ?
C74 C82 C70 102.0(2) . . ?
C91 C82 C78 111.1(2) . . ?
C74 C82 C78 100.7(2) . . ?
C70 C82 C78 110.3(2) . . ?
O24 C83 O25 123.6(3) . . ?
O24 C83 C74 125.7(3) . . ?
O25 C83 C74 110.5(3) . . ?
O26 C84 N80 121.9(3) . . ?
O26 C84 C85 119.7(3) . . ?
N80 C84 C85 118.3(2) . . ?
C90 C85 C86 119.6(3) . . ?
C90 C85 C84 120.2(3) . . ?
C86 C85 C84 120.1(3) . . ?
C87 C86 C85 120.5(3) . . ?
C87 C86 H86 119.8 . . ?
C85 C86 H86 119.8 . . ?
C88 C87 C86 119.7(3) . . ?
C88 C87 H87 120.1 . . ?
C86 C87 H87 120.1 . . ?
C87 C88 C89 119.9(3) . . ?
C87 C88 H88 120.1 . . ?
C89 C88 H88 120.1 . . ?
C90 C89 C88 120.6(3) . . ?
C90 C89 H89 119.7 . . ?
C88 C89 H89 119.7 . . ?
C89 C90 C85 119.7(3) . . ?
C89 C90 H90 120.2 . . ?
C85 C90 H90 120.2 . . ?
O27 C91 O28 123.0(3) . . ?
O27 C91 C82 122.1(3) . . ?
O28 C91 C82 114.7(2) . . ?
O28 C92 H92A 109.5 . . ?
O28 C92 H92B 109.5 . . ?
H92A C92 H92B 109.5 . . ?
O28 C92 H92C 109.5 . . ?
H92A C92 H92C 109.5 . . ?
H92B C92 H92C 109.5 . . ?
C93 O29 C96 96.7(2) . . ?
C98 O30 C101 96.7(2) . . ?
C106 O32 H32O 97.5 . . ?
C114 O35 C115 115.9(2) . . ?
O29 C93 C104 110.4(2) . . ?
O29 C93 C94 100.9(2) . . ?
C104 C93 C94 121.7(2) . . ?
O29 C93 C105 101.7(2) . . ?
C104 C93 C105 112.4(2) . . ?
C94 C93 C105 107.4(2) . . ?
C95 C94 C93 105.0(3) . . ?
C95 C94 H94 127.5 . . ?
C93 C94 H94 127.5 . . ?
C94 C95 C96 105.9(3) . . ?
C94 C95 H95 127.1 . . ?
C96 C95 H95 127.1 . . ?
O29 C96 C95 100.2(2) . . ?
O29 C96 C97 102.0(2) . . ?
C95 C96 C97 107.8(2) . . ?
O29 C96 H96 115.0 . . ?
C95 C96 H96 115.0 . . ?
C97 C96 H96 115.0 . . ?
C106 C97 C105 119.4(2) . . ?
C106 C97 C96 113.8(2) . . ?
C105 C97 C96 100.8(2) . . ?
C106 C97 C98 108.6(2) . . ?
C105 C97 C98 100.1(2) . . ?
C96 C97 C98 113.4(2) . . ?
O30 C98 C99 100.4(2) . . ?
O30 C98 C97 101.3(2) . . ?
C99 C98 C97 108.4(2) . . ?
O30 C98 H98 115.0 . . ?
C99 C98 H98 115.0 . . ?
C97 C98 H98 115.0 . . ?
C100 C99 C98 106.2(3) . . ?
C100 C99 H99 126.9 . . ?
C98 C99 H99 126.9 . . ?
C99 C100 C101 105.0(2) . . ?
C99 C100 H100 127.5 . . ?
C101 C100 H100 127.5 . . ?
O30 C101 C102 110.6(2) . . ?
O30 C101 C100 100.6(2) . . ?
C102 C101 C100 120.6(2) . . ?
O30 C101 C105 101.3(2) . . ?
C102 C101 C105 113.6(2) . . ?
C100 C101 C105 107.7(2) . . ?
N103 C102 C101 110.2(2) . . ?
N103 C102 H10C 109.6 . . ?
C101 C102 H10C 109.6 . . ?
N103 C102 H10D 109.6 . . ?
C101 C102 H10D 109.6 . . ?
H10C C102 H10D 108.1 . . ?
C107 N103 C104 122.7(2) . . ?
C107 N103 C102 118.3(2) . . ?
C104 N103 C102 115.7(2) . . ?
N103 C104 C93 110.6(2) . . ?
N103 C104 H10E 109.5 . . ?
C93 C104 H10E 109.5 . . ?
N103 C104 H10F 109.5 . . ?
C93 C104 H10F 109.5 . . ?
H10E C104 H10F 108.1 . . ?
C114 C105 C97 117.5(3) . . ?
C114 C105 C101 115.8(2) . . ?
C97 C105 C101 101.3(2) . . ?
C114 C105 C93 110.0(2) . . ?
C97 C105 C93 100.5(2) . . ?
C101 C105 C93 110.4(2) . . ?
O31 C106 O32 123.6(3) . . ?
O31 C106 C97 124.0(3) . . ?
O32 C106 C97 112.3(3) . . ?
O33 C107 N103 121.2(3) . . ?
O33 C107 C108 120.0(3) . . ?
N103 C107 C108 118.6(3) . . ?
C113 C108 C109 119.5(3) . . ?
C113 C108 C107 121.0(3) . . ?
C109 C108 C107 119.4(3) . . ?
C108 C109 C110 120.6(3) . . ?
C108 C109 H109 119.7 . . ?
C110 C109 H109 119.7 . . ?
C111 C110 C109 119.8(3) . . ?
C111 C110 H110 120.1 . . ?
C109 C110 H110 120.1 . . ?
C112 C111 C110 119.5(3) . . ?
C112 C111 H111 120.2 . . ?
C110 C111 H111 120.2 . . ?
C111 C112 C113 121.1(3) . . ?
C111 C112 H112 119.5 . . ?
C113 C112 H112 119.5 . . ?
C108 C113 C112 119.4(3) . . ?
C108 C113 H113 120.3 . . ?
C112 C113 H113 120.3 . . ?
O34 C114 O35 122.0(3) . . ?
O34 C114 C105 124.8(3) . . ?
O35 C114 C105 113.1(3) . . ?
O35 C115 H11A 109.5 . . ?
O35 C115 H11B 109.5 . . ?
H11A C115 H11B 109.5 . . ?
O35 C115 H11C 109.5 . . ?
H11A C115 H11C 109.5 . . ?
H11B C115 H11C 109.5 . . ?
C116 O36 C119 96.7(2) . . ?
C124 O37 C121 96.3(2) . . ?
C129 O39 H39O 113.1 . . ?
C137 O42 C138 117.7(3) . . ?
O36 C116 C127 110.5(2) . . ?
O36 C116 C117 101.3(2) . . ?
C127 C116 C117 120.3(2) . . ?
O36 C116 C128 101.2(2) . . ?
C127 C116 C128 113.8(2) . . ?
C117 C116 C128 107.3(2) . . ?
C118 C117 C116 105.2(2) . . ?
C118 C117 H117 127.4 . . ?
C116 C117 H117 127.4 . . ?
C117 C118 C119 106.2(3) . . ?
C117 C118 H118 126.9 . . ?
C119 C118 H118 126.9 . . ?
O36 C119 C118 99.9(2) . . ?
O36 C119 C120 101.3(2) . . ?
C118 C119 C120 108.4(2) . . ?
O36 C119 H119 115.1 . . ?
C118 C119 H119 115.1 . . ?
C120 C119 H119 115.1 . . ?
C129 C120 C128 118.5(2) . . ?
C129 C120 C119 113.4(2) . . ?
C128 C120 C119 100.3(2) . . ?
C129 C120 C121 110.3(2) . . ?
C128 C120 C121 99.2(2) . . ?
C119 C120 C121 114.3(2) . . ?
O37 C121 C122 100.4(2) . . ?
O37 C121 C120 101.9(2) . . ?
C122 C121 C120 108.5(2) . . ?
O37 C121 H121 114.8 . . ?
C122 C121 H121 114.8 . . ?
C120 C121 H121 114.8 . . ?
C123 C122 C121 106.3(2) . . ?
C123 C122 H122 126.8 . . ?
C121 C122 H122 126.8 . . ?
C122 C123 C124 104.8(2) . . ?
C122 C123 H123 127.6 . . ?
C124 C123 H123 127.6 . . ?
O37 C124 C125 110.7(2) . . ?
O37 C124 C123 100.9(2) . . ?
C125 C124 C123 120.2(2) . . ?
O37 C124 C128 101.5(2) . . ?
C125 C124 C128 114.5(2) . . ?
C123 C124 C128 106.7(2) . . ?
N126 C125 C124 111.3(2) . . ?
N126 C125 H12C 109.4 . . ?
C124 C125 H12C 109.4 . . ?
N126 C125 H12D 109.4 . . ?
C124 C125 H12D 109.4 . . ?
H12C C125 H12D 108.0 . . ?
C130 N126 C127 123.8(2) . . ?
C130 N126 C125 119.5(2) . . ?
C127 N126 C125 115.8(2) . . ?
N126 C127 C116 110.9(2) . . ?
N126 C127 H12E 109.5 . . ?
C116 C127 H12E 109.5 . . ?
N126 C127 H12F 109.5 . . ?
C116 C127 H12F 109.5 . . ?
H12E C127 H12F 108.1 . . ?
C137 C128 C120 116.9(2) . . ?
C137 C128 C124 115.0(2) . . ?
C120 C128 C124 102.1(2) . . ?
C137 C128 C116 111.1(2) . . ?
C120 C128 C116 101.1(2) . . ?
C124 C128 C116 109.4(2) . . ?
O38 C129 O39 122.5(3) . . ?
O38 C129 C120 124.1(3) . . ?
O39 C129 C120 113.2(2) . . ?
O40 C130 N126 121.2(3) . . ?
O40 C130 C131 120.0(3) . . ?
N126 C130 C131 118.6(3) . . ?
C132 C131 C136 120.0(3) . . ?
C132 C131 C130 120.2(3) . . ?
C136 C131 C130 119.6(3) . . ?
C133 C132 C131 120.3(3) . . ?
C133 C132 H132 119.8 . . ?
C131 C132 H132 119.8 . . ?
C134 C133 C132 120.0(3) . . ?
C134 C133 H133 120.0 . . ?
C132 C133 H133 120.0 . . ?
C133 C134 C135 120.0(3) . . ?
C133 C134 H134 120.0 . . ?
C135 C134 H134 120.0 . . ?
C136 C135 C134 120.5(3) . . ?
C136 C135 H135 119.8 . . ?
C134 C135 H135 119.8 . . ?
C135 C136 C131 119.1(3) . . ?
C135 C136 H136 120.4 . . ?
C131 C136 H136 120.4 . . ?
O41 C137 O42 123.3(3) . . ?
O41 C137 C128 125.6(3) . . ?
O42 C137 C128 111.1(3) . . ?
O42 C138 H13A 109.5 . . ?
O42 C138 H13B 109.5 . . ?
H13A C138 H13B 109.5 . . ?
O42 C138 H13C 109.5 . . ?
H13A C138 H13C 109.5 . . ?
H13B C138 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O1 C1 C12 178.3(2) . . . . ?
C4 O1 C1 C2 -51.6(2) . . . . ?
C4 O1 C1 C13 58.5(2) . . . . ?
O1 C1 C2 C3 33.0(3) . . . . ?
C12 C1 C2 C3 155.3(3) . . . . ?
C13 C1 C2 C3 -72.1(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C1 O1 C4 C3 51.3(2) . . . . ?
C1 O1 C4 C5 -59.6(2) . . . . ?
C2 C3 C4 O1 -32.6(3) . . . . ?
C2 C3 C4 C5 73.9(3) . . . . ?
O1 C4 C5 C14 163.4(2) . . . . ?
C3 C4 C5 C14 58.3(3) . . . . ?
O1 C4 C5 C13 35.6(3) . . . . ?
C3 C4 C5 C13 -69.5(3) . . . . ?
O1 C4 C5 C6 -70.1(3) . . . . ?
C3 C4 C5 C6 -175.3(2) . . . . ?
C9 O2 C6 C7 -51.1(2) . . . . ?
C9 O2 C6 C5 60.4(2) . . . . ?
C14 C5 C6 O2 -164.0(2) . . . . ?
C13 C5 C6 O2 -38.3(2) . . . . ?
C4 C5 C6 O2 67.8(3) . . . . ?
C14 C5 C6 C7 -59.1(3) . . . . ?
C13 C5 C6 C7 66.7(3) . . . . ?
C4 C5 C6 C7 172.8(2) . . . . ?
O2 C6 C7 C8 31.7(3) . . . . ?
C5 C6 C7 C8 -74.1(3) . . . . ?
C6 C7 C8 C9 1.3(3) . . . . ?
C6 O2 C9 C10 -179.1(2) . . . . ?
C6 O2 C9 C8 52.1(2) . . . . ?
C6 O2 C9 C13 -57.4(2) . . . . ?
C7 C8 C9 O2 -33.9(3) . . . . ?
C7 C8 C9 C10 -155.9(3) . . . . ?
C7 C8 C9 C13 71.2(3) . . . . ?
O2 C9 C10 N11 63.4(3) . . . . ?
C8 C9 C10 N11 -179.8(2) . . . . ?
C13 C9 C10 N11 -50.2(3) . . . . ?
C9 C10 N11 C15 -105.5(3) . . . . ?
C9 C10 N11 C12 57.9(3) . . . . ?
C15 N11 C12 C1 103.3(3) . . . . ?
C10 N11 C12 C1 -59.4(3) . . . . ?
O1 C1 C12 N11 -59.5(3) . . . . ?
C2 C1 C12 N11 -177.3(2) . . . . ?
C13 C1 C12 N11 52.6(3) . . . . ?
C14 C5 C13 C22 -4.9(4) . . . . ?
C4 C5 C13 C22 119.1(3) . . . . ?
C6 C5 C13 C22 -124.3(3) . . . . ?
C14 C5 C13 C9 122.6(3) . . . . ?
C4 C5 C13 C9 -113.3(2) . . . . ?
C6 C5 C13 C9 3.2(3) . . . . ?
C14 C5 C13 C1 -124.2(3) . . . . ?
C4 C5 C13 C1 -0.1(3) . . . . ?
C6 C5 C13 C1 116.4(2) . . . . ?
O2 C9 C13 C22 161.5(2) . . . . ?
C10 C9 C13 C22 -79.3(3) . . . . ?
C8 C9 C13 C22 57.0(3) . . . . ?
O2 C9 C13 C5 32.5(2) . . . . ?
C10 C9 C13 C5 151.7(2) . . . . ?
C8 C9 C13 C5 -72.0(2) . . . . ?
O2 C9 C13 C1 -74.1(2) . . . . ?
C10 C9 C13 C1 45.1(3) . . . . ?
C8 C9 C13 C1 -178.6(2) . . . . ?
O1 C1 C13 C22 -160.5(2) . . . . ?
C12 C1 C13 C22 81.8(3) . . . . ?
C2 C1 C13 C22 -55.4(3) . . . . ?
O1 C1 C13 C5 -35.5(3) . . . . ?
C12 C1 C13 C5 -153.2(2) . . . . ?
C2 C1 C13 C5 69.6(3) . . . . ?
O1 C1 C13 C9 71.6(3) . . . . ?
C12 C1 C13 C9 -46.1(3) . . . . ?
C2 C1 C13 C9 176.8(2) . . . . ?
C13 C5 C14 O3 -52.7(4) . . . . ?
C4 C5 C14 O3 -170.3(3) . . . . ?
C6 C5 C14 O3 61.3(4) . . . . ?
C13 C5 C14 O4 131.0(3) . . . . ?
C4 C5 C14 O4 13.5(3) . . . . ?
C6 C5 C14 O4 -114.9(3) . . . . ?
C12 N11 C15 O5 -162.9(3) . . . . ?
C10 N11 C15 O5 -0.8(4) . . . . ?
C12 N11 C15 C16 21.9(4) . . . . ?
C10 N11 C15 C16 -176.1(3) . . . . ?
O5 C15 C16 C21 83.4(4) . . . . ?
N11 C15 C16 C21 -101.3(4) . . . . ?
O5 C15 C16 C17 -91.4(4) . . . . ?
N11 C15 C16 C17 83.9(4) . . . . ?
C21 C16 C17 C18 0.7(5) . . . . ?
C15 C16 C17 C18 175.6(3) . . . . ?
C16 C17 C18 C19 -1.0(5) . . . . ?
C17 C18 C19 C20 0.5(5) . . . . ?
C18 C19 C20 C21 0.2(6) . . . . ?
C17 C16 C21 C20 0.1(6) . . . . ?
C15 C16 C21 C20 -174.7(3) . . . . ?
C19 C20 C21 C16 -0.5(6) . . . . ?
C23 O7 C22 O6 2.0(4) . . . . ?
C23 O7 C22 C13 178.0(2) . . . . ?
C5 C13 C22 O6 -41.3(4) . . . . ?
C9 C13 C22 O6 -162.0(3) . . . . ?
C1 C13 C22 O6 73.4(4) . . . . ?
C5 C13 C22 O7 142.9(2) . . . . ?
C9 C13 C22 O7 22.1(3) . . . . ?
C1 C13 C22 O7 -102.4(3) . . . . ?
C27 O8 C24 C35 179.5(2) . . . . ?
C27 O8 C24 C25 -52.3(2) . . . . ?
C27 O8 C24 C36 58.3(2) . . . . ?
O8 C24 C25 C26 33.5(3) . . . . ?
C35 C24 C25 C26 154.6(3) . . . . ?
C36 C24 C25 C26 -72.5(3) . . . . ?
C24 C25 C26 C27 -0.2(3) . . . . ?
C24 O8 C27 C26 51.4(2) . . . . ?
C24 O8 C27 C28 -59.9(2) . . . . ?
C25 C26 C27 O8 -32.5(3) . . . . ?
C25 C26 C27 C28 73.6(3) . . . . ?
O8 C27 C28 C37 164.8(2) . . . . ?
C26 C27 C28 C37 60.2(3) . . . . ?
O8 C27 C28 C36 36.6(2) . . . . ?
C26 C27 C28 C36 -68.1(3) . . . . ?
O8 C27 C28 C29 -68.5(3) . . . . ?
C26 C27 C28 C29 -173.1(2) . . . . ?
C32 O9 C29 C30 -51.1(2) . . . . ?
C32 O9 C29 C28 60.6(2) . . . . ?
C37 C28 C29 O9 -164.1(2) . . . . ?
C36 C28 C29 O9 -38.2(2) . . . . ?
C27 C28 C29 O9 67.2(3) . . . . ?
C37 C28 C29 C30 -59.0(3) . . . . ?
C36 C28 C29 C30 66.9(3) . . . . ?
C27 C28 C29 C30 172.3(2) . . . . ?
O9 C29 C30 C31 31.8(3) . . . . ?
C28 C29 C30 C31 -74.5(3) . . . . ?
C29 C30 C31 C32 1.1(3) . . . . ?
C29 O9 C32 C33 -179.7(2) . . . . ?
C29 O9 C32 C31 52.2(2) . . . . ?
C29 O9 C32 C36 -57.2(2) . . . . ?
C30 C31 C32 O9 -33.8(3) . . . . ?
C30 C31 C32 C33 -155.7(3) . . . . ?
C30 C31 C32 C36 71.4(3) . . . . ?
O9 C32 C33 N34 63.4(3) . . . . ?
C31 C32 C33 N34 -179.9(2) . . . . ?
C36 C32 C33 N34 -50.7(3) . . . . ?
C32 C33 N34 C38 -112.5(3) . . . . ?
C32 C33 N34 C35 56.8(3) . . . . ?
C38 N34 C35 C24 111.4(3) . . . . ?
C33 N34 C35 C24 -57.3(3) . . . . ?
O8 C24 C35 N34 -61.9(3) . . . . ?
C25 C24 C35 N34 -178.6(2) . . . . ?
C36 C24 C35 N34 51.4(3) . . . . ?
C37 C28 C36 C45 -3.9(4) . . . . ?
C29 C28 C36 C45 -122.5(2) . . . . ?
C27 C28 C36 C45 120.2(2) . . . . ?
C37 C28 C36 C32 121.8(3) . . . . ?
C29 C28 C36 C32 3.2(3) . . . . ?
C27 C28 C36 C32 -114.1(2) . . . . ?
C37 C28 C36 C24 -125.5(3) . . . . ?
C29 C28 C36 C24 115.9(2) . . . . ?
C27 C28 C36 C24 -1.4(3) . . . . ?
O9 C32 C36 C45 159.4(2) . . . . ?
C33 C32 C36 C45 -81.1(3) . . . . ?
C31 C32 C36 C45 54.6(3) . . . . ?
O9 C32 C36 C28 32.6(3) . . . . ?
C33 C32 C36 C28 152.0(2) . . . . ?
C31 C32 C36 C28 -72.3(2) . . . . ?
O9 C32 C36 C24 -74.2(2) . . . . ?
C33 C32 C36 C24 45.3(3) . . . . ?
C31 C32 C36 C24 -179.1(2) . . . . ?
O8 C24 C36 C45 -159.3(2) . . . . ?
C35 C24 C36 C45 82.6(3) . . . . ?
C25 C24 C36 C45 -53.6(3) . . . . ?
O8 C24 C36 C28 -34.7(3) . . . . ?
C35 C24 C36 C28 -152.7(2) . . . . ?
C25 C24 C36 C28 71.1(3) . . . . ?
O8 C24 C36 C32 72.8(3) . . . . ?
C35 C24 C36 C32 -45.3(3) . . . . ?
C25 C24 C36 C32 178.5(2) . . . . ?
C36 C28 C37 O10 -71.3(4) . . . . ?
C29 C28 C37 O10 41.9(4) . . . . ?
C27 C28 C37 O10 171.4(3) . . . . ?
C36 C28 C37 O11 113.1(3) . . . . ?
C29 C28 C37 O11 -133.7(2) . . . . ?
C27 C28 C37 O11 -4.2(3) . . . . ?
C35 N34 C38 O12 -166.1(3) . . . . ?
C33 N34 C38 O12 2.2(4) . . . . ?
C35 N34 C38 C39 17.1(4) . . . . ?
C33 N34 C38 C39 -174.6(2) . . . . ?
O12 C38 C39 C44 53.8(4) . . . . ?
N34 C38 C39 C44 -129.4(3) . . . . ?
O12 C38 C39 C40 -121.0(3) . . . . ?
N34 C38 C39 C40 55.9(4) . . . . ?
C44 C39 C40 C41 0.8(5) . . . . ?
C38 C39 C40 C41 175.4(3) . . . . ?
C39 C40 C41 C42 1.1(5) . . . . ?
C40 C41 C42 C43 -1.5(5) . . . . ?
C41 C42 C43 C44 0.0(5) . . . . ?
C40 C39 C44 C43 -2.3(5) . . . . ?
C38 C39 C44 C43 -177.1(3) . . . . ?
C42 C43 C44 C39 1.9(5) . . . . ?
C46 O14 C45 O13 5.4(4) . . . . ?
C46 O14 C45 C36 -176.1(2) . . . . ?
C28 C36 C45 O13 -28.4(4) . . . . ?
C32 C36 C45 O13 -147.7(3) . . . . ?
C24 C36 C45 O13 87.4(4) . . . . ?
C28 C36 C45 O14 153.2(2) . . . . ?
C32 C36 C45 O14 33.9(3) . . . . ?
C24 C36 C45 O14 -91.0(3) . . . . ?
C50 O15 C47 C58 179.3(2) . . . . ?
C50 O15 C47 C48 -51.9(2) . . . . ?
C50 O15 C47 C59 58.0(2) . . . . ?
O15 C47 C48 C49 33.8(3) . . . . ?
C58 C47 C48 C49 155.4(3) . . . . ?
C59 C47 C48 C49 -72.1(3) . . . . ?
C47 C48 C49 C50 -1.0(3) . . . . ?
C47 O15 C50 C49 51.0(2) . . . . ?
C47 O15 C50 C51 -59.8(2) . . . . ?
C48 C49 C50 O15 -31.9(3) . . . . ?
C48 C49 C50 C51 74.4(3) . . . . ?
O15 C50 C51 C60 163.0(2) . . . . ?
C49 C50 C51 C60 57.8(3) . . . . ?
O15 C50 C51 C59 37.0(2) . . . . ?
C49 C50 C51 C59 -68.3(3) . . . . ?
O15 C50 C51 C52 -69.0(3) . . . . ?
C49 C50 C51 C52 -174.2(2) . . . . ?
C55 O16 C52 C53 -51.0(2) . . . . ?
C55 O16 C52 C51 58.9(2) . . . . ?
C60 C51 C52 O16 -165.0(2) . . . . ?
C59 C51 C52 O16 -35.0(2) . . . . ?
C50 C51 C52 O16 70.1(3) . . . . ?
C60 C51 C52 C53 -60.3(3) . . . . ?
C59 C51 C52 C53 69.7(3) . . . . ?
C50 C51 C52 C53 174.7(2) . . . . ?
O16 C52 C53 C54 32.1(3) . . . . ?
C51 C52 C53 C54 -73.5(3) . . . . ?
C52 C53 C54 C55 0.3(3) . . . . ?
C52 O16 C55 C56 -178.5(2) . . . . ?
C52 O16 C55 C54 51.6(2) . . . . ?
C52 O16 C55 C59 -58.9(2) . . . . ?
C53 C54 C55 O16 -32.7(3) . . . . ?
C53 C54 C55 C56 -156.1(3) . . . . ?
C53 C54 C55 C59 73.1(3) . . . . ?
O16 C55 C56 N57 60.4(3) . . . . ?
C54 C55 C56 N57 178.8(2) . . . . ?
C59 C55 C56 N57 -52.5(3) . . . . ?
C55 C56 N57 C61 -106.3(3) . . . . ?
C55 C56 N57 C58 58.6(3) . . . . ?
C61 N57 C58 C47 108.2(3) . . . . ?
C56 N57 C58 C47 -56.1(3) . . . . ?
O15 C47 C58 N57 -63.7(3) . . . . ?
C48 C47 C58 N57 179.3(2) . . . . ?
C59 C47 C58 N57 49.9(3) . . . . ?
C60 C51 C59 C68 2.1(4) . . . . ?
C52 C51 C59 C68 -124.4(3) . . . . ?
C50 C51 C59 C68 120.2(3) . . . . ?
C60 C51 C59 C47 -119.9(3) . . . . ?
C52 C51 C59 C47 113.6(2) . . . . ?
C50 C51 C59 C47 -1.7(2) . . . . ?
C60 C51 C59 C55 126.3(3) . . . . ?
C52 C51 C59 C55 -0.2(2) . . . . ?
C50 C51 C59 C55 -115.5(2) . . . . ?
O15 C47 C59 C68 -165.8(2) . . . . ?
C58 C47 C59 C68 75.6(3) . . . . ?
C48 C47 C59 C68 -60.4(3) . . . . ?
O15 C47 C59 C51 -34.1(3) . . . . ?
C58 C47 C59 C51 -152.6(2) . . . . ?
C48 C47 C59 C51 71.3(3) . . . . ?
O15 C47 C59 C55 72.1(3) . . . . ?
C58 C47 C59 C55 -46.4(3) . . . . ?
C48 C47 C59 C55 177.5(2) . . . . ?
O16 C55 C59 C68 167.8(2) . . . . ?
C56 C55 C59 C68 -73.3(3) . . . . ?
C54 C55 C59 C68 62.3(3) . . . . ?
O16 C55 C59 C51 35.4(2) . . . . ?
C56 C55 C59 C51 154.3(2) . . . . ?
C54 C55 C59 C51 -70.1(2) . . . . ?
O16 C55 C59 C47 -71.7(2) . . . . ?
C56 C55 C59 C47 47.2(3) . . . . ?
C54 C55 C59 C47 -177.2(2) . . . . ?
C59 C51 C60 O17 31.2(4) . . . . ?
C52 C51 C60 O17 151.0(3) . . . . ?
C50 C51 C60 O17 -82.1(3) . . . . ?
C59 C51 C60 O18 -153.4(2) . . . . ?
C52 C51 C60 O18 -33.6(3) . . . . ?
C50 C51 C60 O18 93.3(3) . . . . ?
C58 N57 C61 O19 -156.3(3) . . . . ?
C56 N57 C61 O19 7.5(4) . . . . ?
C58 N57 C61 C62 28.0(4) . . . . ?
C56 N57 C61 C62 -168.3(3) . . . . ?
O19 C61 C62 C67 49.1(4) . . . . ?
N57 C61 C62 C67 -135.1(3) . . . . ?
O19 C61 C62 C63 -127.4(3) . . . . ?
N57 C61 C62 C63 48.4(4) . . . . ?
C67 C62 C63 C64 2.8(5) . . . . ?
C61 C62 C63 C64 179.3(3) . . . . ?
C62 C63 C64 C65 -0.2(5) . . . . ?
C63 C64 C65 C66 -2.1(5) . . . . ?
C64 C65 C66 C67 1.6(5) . . . . ?
C63 C62 C67 C66 -3.2(5) . . . . ?
C61 C62 C67 C66 -179.7(3) . . . . ?
C65 C66 C67 C62 1.0(5) . . . . ?
C69 O21 C68 O20 -0.2(4) . . . . ?
C69 O21 C68 C59 173.6(2) . . . . ?
C51 C59 C68 O20 -134.4(3) . . . . ?
C47 C59 C68 O20 -15.6(4) . . . . ?
C55 C59 C68 O20 106.1(3) . . . . ?
C51 C59 C68 O21 51.7(4) . . . . ?
C47 C59 C68 O21 170.6(2) . . . . ?
C55 C59 C68 O21 -67.7(3) . . . . ?
C73 O22 C70 C81 179.8(2) . . . . ?
C73 O22 C70 C71 -51.7(2) . . . . ?
C73 O22 C70 C82 57.7(2) . . . . ?
O22 C70 C71 C72 33.5(3) . . . . ?
C81 C70 C71 C72 155.2(3) . . . . ?
C82 C70 C71 C72 -72.1(3) . . . . ?
C70 C71 C72 C73 -1.0(3) . . . . ?
C70 O22 C73 C72 50.8(2) . . . . ?
C70 O22 C73 C74 -59.3(2) . . . . ?
C71 C72 C73 O22 -31.7(3) . . . . ?
C71 C72 C73 C74 74.6(3) . . . . ?
O22 C73 C74 C83 162.9(2) . . . . ?
C72 C73 C74 C83 57.7(3) . . . . ?
O22 C73 C74 C82 36.5(3) . . . . ?
C72 C73 C74 C82 -68.6(3) . . . . ?
O22 C73 C74 C75 -69.4(3) . . . . ?
C72 C73 C74 C75 -174.5(3) . . . . ?
C78 O23 C75 C76 -51.1(2) . . . . ?
C78 O23 C75 C74 58.8(2) . . . . ?
C83 C74 C75 O23 -165.6(2) . . . . ?
C82 C74 C75 O23 -35.2(2) . . . . ?
C73 C74 C75 O23 69.9(3) . . . . ?
C83 C74 C75 C76 -61.0(3) . . . . ?
C82 C74 C75 C76 69.4(3) . . . . ?
C73 C74 C75 C76 174.5(2) . . . . ?
O23 C75 C76 C77 32.1(3) . . . . ?
C74 C75 C76 C77 -73.5(3) . . . . ?
C75 C76 C77 C78 0.3(3) . . . . ?
C75 O23 C78 C79 -178.3(2) . . . . ?
C75 O23 C78 C77 51.8(2) . . . . ?
C75 O23 C78 C82 -58.7(2) . . . . ?
C76 C77 C78 O23 -32.9(3) . . . . ?
C76 C77 C78 C79 -156.1(3) . . . . ?
C76 C77 C78 C82 73.0(3) . . . . ?
O23 C78 C79 N80 61.5(3) . . . . ?
C77 C78 C79 N80 179.7(2) . . . . ?
C82 C78 C79 N80 -51.5(3) . . . . ?
C78 C79 N80 C84 -112.3(3) . . . . ?
C78 C79 N80 C81 57.5(3) . . . . ?
C84 N80 C81 C70 114.0(3) . . . . ?
C79 N80 C81 C70 -55.5(3) . . . . ?
O22 C70 C81 N80 -63.9(3) . . . . ?
C71 C70 C81 N80 179.1(2) . . . . ?
C82 C70 C81 N80 50.1(3) . . . . ?
C83 C74 C82 C91 2.7(4) . . . . ?
C75 C74 C82 C91 -124.1(3) . . . . ?
C73 C74 C82 C91 120.8(3) . . . . ?
C83 C74 C82 C70 -119.4(3) . . . . ?
C75 C74 C82 C70 113.8(2) . . . . ?
C73 C74 C82 C70 -1.3(3) . . . . ?
C83 C74 C82 C78 126.9(3) . . . . ?
C75 C74 C82 C78 0.1(2) . . . . ?
C73 C74 C82 C78 -115.0(2) . . . . ?
O22 C70 C82 C91 -165.7(2) . . . . ?
C81 C70 C82 C91 75.2(3) . . . . ?
C71 C70 C82 C91 -60.6(3) . . . . ?
O22 C70 C82 C74 -34.0(3) . . . . ?
C81 C70 C82 C74 -153.1(2) . . . . ?
C71 C70 C82 C74 71.1(3) . . . . ?
O22 C70 C82 C78 72.3(3) . . . . ?
C81 C70 C82 C78 -46.8(3) . . . . ?
C71 C70 C82 C78 177.4(2) . . . . ?
O23 C78 C82 C91 167.3(2) . . . . ?
C79 C78 C82 C91 -73.8(3) . . . . ?
C77 C78 C82 C91 61.9(3) . . . . ?
O23 C78 C82 C74 35.1(3) . . . . ?
C79 C78 C82 C74 153.9(2) . . . . ?
C77 C78 C82 C74 -70.3(2) . . . . ?
O23 C78 C82 C70 -72.1(3) . . . . ?
C79 C78 C82 C70 46.7(3) . . . . ?
C77 C78 C82 C70 -177.5(2) . . . . ?
C82 C74 C83 O24 30.8(4) . . . . ?
C75 C74 C83 O24 150.9(3) . . . . ?
C73 C74 C83 O24 -82.6(4) . . . . ?
C82 C74 C83 O25 -153.6(2) . . . . ?
C75 C74 C83 O25 -33.5(3) . . . . ?
C73 C74 C83 O25 93.0(3) . . . . ?
C81 N80 C84 O26 -160.3(3) . . . . ?
C79 N80 C84 O26 8.8(4) . . . . ?
C81 N80 C84 C85 23.5(4) . . . . ?
C79 N80 C84 C85 -167.3(3) . . . . ?
O26 C84 C85 C90 49.5(4) . . . . ?
N80 C84 C85 C90 -134.3(3) . . . . ?
O26 C84 C85 C86 -126.4(3) . . . . ?
N80 C84 C85 C86 49.9(4) . . . . ?
C90 C85 C86 C87 2.0(5) . . . . ?
C84 C85 C86 C87 177.8(3) . . . . ?
C85 C86 C87 C88 0.3(5) . . . . ?
C86 C87 C88 C89 -2.3(5) . . . . ?
C87 C88 C89 C90 2.0(5) . . . . ?
C88 C89 C90 C85 0.3(5) . . . . ?
C86 C85 C90 C89 -2.2(5) . . . . ?
C84 C85 C90 C89 -178.1(3) . . . . ?
C92 O28 C91 O27 2.1(4) . . . . ?
C92 O28 C91 C82 177.3(2) . . . . ?
C74 C82 C91 O27 -136.0(3) . . . . ?
C70 C82 C91 O27 -17.0(4) . . . . ?
C78 C82 C91 O27 104.5(3) . . . . ?
C74 C82 C91 O28 48.7(4) . . . . ?
C70 C82 C91 O28 167.7(3) . . . . ?
C78 C82 C91 O28 -70.7(3) . . . . ?
C96 O29 C93 C104 177.6(2) . . . . ?
C96 O29 C93 C94 -52.4(2) . . . . ?
C96 O29 C93 C105 58.1(2) . . . . ?
O29 C93 C94 C95 33.5(3) . . . . ?
C104 C93 C94 C95 155.9(3) . . . . ?
C105 C93 C94 C95 -72.5(3) . . . . ?
C93 C94 C95 C96 -0.5(3) . . . . ?
C93 O29 C96 C95 51.7(2) . . . . ?
C93 O29 C96 C97 -59.2(2) . . . . ?
C94 C95 C96 O29 -32.4(3) . . . . ?
C94 C95 C96 C97 73.9(3) . . . . ?
O29 C96 C97 C106 165.0(2) . . . . ?
C95 C96 C97 C106 60.1(3) . . . . ?
O29 C96 C97 C105 35.9(3) . . . . ?
C95 C96 C97 C105 -69.0(3) . . . . ?
O29 C96 C97 C98 -70.2(3) . . . . ?
C95 C96 C97 C98 -175.1(2) . . . . ?
C101 O30 C98 C99 -51.1(2) . . . . ?
C101 O30 C98 C97 60.2(2) . . . . ?
C106 C97 C98 O30 -163.4(2) . . . . ?
C105 C97 C98 O30 -37.5(2) . . . . ?
C96 C97 C98 O30 69.1(3) . . . . ?
C106 C97 C98 C99 -58.3(3) . . . . ?
C105 C97 C98 C99 67.6(3) . . . . ?
C96 C97 C98 C99 174.1(2) . . . . ?
O30 C98 C99 C100 31.7(3) . . . . ?
C97 C98 C99 C100 -74.0(3) . . . . ?
C98 C99 C100 C101 1.3(3) . . . . ?
C98 O30 C101 C102 -179.2(2) . . . . ?
C98 O30 C101 C100 52.2(2) . . . . ?
C98 O30 C101 C105 -58.4(2) . . . . ?
C99 C100 C101 O30 -33.8(3) . . . . ?
C99 C100 C101 C102 -155.6(3) . . . . ?
C99 C100 C101 C105 71.8(3) . . . . ?
O30 C101 C102 N103 61.8(3) . . . . ?
C100 C101 C102 N103 178.6(2) . . . . ?
C105 C101 C102 N103 -51.4(3) . . . . ?
C101 C102 N103 C107 -100.9(3) . . . . ?
C101 C102 N103 C104 59.0(3) . . . . ?
C107 N103 C104 C93 99.2(3) . . . . ?
C102 N103 C104 C93 -59.7(3) . . . . ?
O29 C93 C104 N103 -60.7(3) . . . . ?
C94 C93 C104 N103 -178.5(2) . . . . ?
C105 C93 C104 N103 52.1(3) . . . . ?
C106 C97 C105 C114 -7.0(4) . . . . ?
C96 C97 C105 C114 118.4(3) . . . . ?
C98 C97 C105 C114 -125.2(3) . . . . ?
C106 C97 C105 C101 120.2(3) . . . . ?
C96 C97 C105 C101 -114.4(2) . . . . ?
C98 C97 C105 C101 2.1(3) . . . . ?
C106 C97 C105 C93 -126.3(3) . . . . ?
C96 C97 C105 C93 -0.8(3) . . . . ?
C98 C97 C105 C93 115.6(2) . . . . ?
O30 C101 C105 C114 162.0(2) . . . . ?
C102 C101 C105 C114 -79.3(3) . . . . ?
C100 C101 C105 C114 56.9(3) . . . . ?
O30 C101 C105 C97 33.7(3) . . . . ?
C102 C101 C105 C97 152.3(2) . . . . ?
C100 C101 C105 C97 -71.5(3) . . . . ?
O30 C101 C105 C93 -72.2(3) . . . . ?
C102 C101 C105 C93 46.5(3) . . . . ?
C100 C101 C105 C93 -177.3(2) . . . . ?
O29 C93 C105 C114 -159.3(2) . . . . ?
C104 C93 C105 C114 82.7(3) . . . . ?
C94 C93 C105 C114 -53.8(3) . . . . ?
O29 C93 C105 C97 -34.7(3) . . . . ?
C104 C93 C105 C97 -152.7(2) . . . . ?
C94 C93 C105 C97 70.8(3) . . . . ?
O29 C93 C105 C101 71.7(3) . . . . ?
C104 C93 C105 C101 -46.4(3) . . . . ?
C94 C93 C105 C101 177.1(2) . . . . ?
C105 C97 C106 O31 -40.3(4) . . . . ?
C96 C97 C106 O31 -159.3(3) . . . . ?
C98 C97 C106 O31 73.4(4) . . . . ?
C105 C97 C106 O32 144.1(3) . . . . ?
C96 C97 C106 O32 25.2(4) . . . . ?
C98 C97 C106 O32 -102.2(3) . . . . ?
C104 N103 C107 O33 -158.9(3) . . . . ?
C102 N103 C107 O33 -0.5(4) . . . . ?
C104 N103 C107 C108 26.5(4) . . . . ?
C102 N103 C107 C108 -175.1(3) . . . . ?
O33 C107 C108 C113 73.6(5) . . . . ?
N103 C107 C108 C113 -111.7(4) . . . . ?
O33 C107 C108 C109 -102.2(4) . . . . ?
N103 C107 C108 C109 72.4(4) . . . . ?
C113 C108 C109 C110 2.3(5) . . . . ?
C107 C108 C109 C110 178.2(3) . . . . ?
C108 C109 C110 C111 -1.0(5) . . . . ?
C109 C110 C111 C112 -0.7(6) . . . . ?
C110 C111 C112 C113 1.1(6) . . . . ?
C109 C108 C113 C112 -1.8(6) . . . . ?
C107 C108 C113 C112 -177.7(4) . . . . ?
C111 C112 C113 C108 0.1(6) . . . . ?
C115 O35 C114 O34 1.6(5) . . . . ?
C115 O35 C114 C105 178.2(2) . . . . ?
C97 C105 C114 O34 -49.1(4) . . . . ?
C101 C105 C114 O34 -168.9(3) . . . . ?
C93 C105 C114 O34 65.0(4) . . . . ?
C97 C105 C114 O35 134.5(3) . . . . ?
C101 C105 C114 O35 14.6(4) . . . . ?
C93 C105 C114 O35 -111.4(3) . . . . ?
C119 O36 C116 C127 179.7(2) . . . . ?
C119 O36 C116 C117 -51.6(2) . . . . ?
C119 O36 C116 C128 58.8(2) . . . . ?
O36 C116 C117 C118 32.8(3) . . . . ?
C127 C116 C117 C118 154.9(3) . . . . ?
C128 C116 C117 C118 -72.9(3) . . . . ?
C116 C117 C118 C119 0.3(3) . . . . ?
C116 O36 C119 C118 51.1(2) . . . . ?
C116 O36 C119 C120 -60.0(2) . . . . ?
C117 C118 C119 O36 -32.5(3) . . . . ?
C117 C118 C119 C120 73.0(3) . . . . ?
O36 C119 C120 C129 163.6(2) . . . . ?
C118 C119 C120 C129 59.1(3) . . . . ?
O36 C119 C120 C128 36.3(2) . . . . ?
C118 C119 C120 C128 -68.3(3) . . . . ?
O36 C119 C120 C121 -68.8(3) . . . . ?
C118 C119 C120 C121 -173.4(2) . . . . ?
C124 O37 C121 C122 -51.1(2) . . . . ?
C124 O37 C121 C120 60.5(2) . . . . ?
C129 C120 C121 O37 -163.3(2) . . . . ?
C128 C120 C121 O37 -38.3(2) . . . . ?
C119 C120 C121 O37 67.5(3) . . . . ?
C129 C120 C121 C122 -58.0(3) . . . . ?
C128 C120 C121 C122 67.1(3) . . . . ?
C119 C120 C121 C122 172.9(2) . . . . ?
O37 C121 C122 C123 31.8(3) . . . . ?
C120 C121 C122 C123 -74.7(3) . . . . ?
C121 C122 C123 C124 1.3(3) . . . . ?
C121 O37 C124 C125 -179.4(2) . . . . ?
C121 O37 C124 C123 52.3(2) . . . . ?
C121 O37 C124 C128 -57.4(2) . . . . ?
C122 C123 C124 O37 -34.1(3) . . . . ?
C122 C123 C124 C125 -155.9(3) . . . . ?
C122 C123 C124 C128 71.5(3) . . . . ?
O37 C124 C125 N126 63.8(3) . . . . ?
C123 C124 C125 N126 -179.2(2) . . . . ?
C128 C124 C125 N126 -50.1(3) . . . . ?
C124 C125 N126 C130 -113.4(3) . . . . ?
C124 C125 N126 C127 56.2(3) . . . . ?
C130 N126 C127 C116 112.0(3) . . . . ?
C125 N126 C127 C116 -57.2(3) . . . . ?
O36 C116 C127 N126 -61.3(3) . . . . ?
C117 C116 C127 N126 -178.8(2) . . . . ?
C128 C116 C127 N126 51.8(3) . . . . ?
C129 C120 C128 C137 -4.3(3) . . . . ?
C119 C120 C128 C137 119.7(2) . . . . ?
C121 C120 C128 C137 -123.4(2) . . . . ?
C129 C120 C128 C124 122.2(2) . . . . ?
C119 C120 C128 C124 -113.9(2) . . . . ?
C121 C120 C128 C124 3.0(2) . . . . ?
C129 C120 C128 C116 -125.0(2) . . . . ?
C119 C120 C128 C116 -1.1(3) . . . . ?
C121 C120 C128 C116 115.8(2) . . . . ?
O37 C124 C128 C137 160.5(2) . . . . ?
C125 C124 C128 C137 -80.2(3) . . . . ?
C123 C124 C128 C137 55.3(3) . . . . ?
O37 C124 C128 C120 32.8(2) . . . . ?
C125 C124 C128 C120 152.1(2) . . . . ?
C123 C124 C128 C120 -72.4(2) . . . . ?
O37 C124 C128 C116 -73.7(2) . . . . ?
C125 C124 C128 C116 45.6(3) . . . . ?
C123 C124 C128 C116 -178.8(2) . . . . ?
O36 C116 C128 C137 -159.7(2) . . . . ?
C127 C116 C128 C137 81.7(3) . . . . ?
C117 C116 C128 C137 -54.0(3) . . . . ?
O36 C116 C128 C120 -35.0(3) . . . . ?
C127 C116 C128 C120 -153.5(2) . . . . ?
C117 C116 C128 C120 70.8(2) . . . . ?
O36 C116 C128 C124 72.2(2) . . . . ?
C127 C116 C128 C124 -46.4(3) . . . . ?
C117 C116 C128 C124 178.0(2) . . . . ?
C128 C120 C129 O38 -68.4(4) . . . . ?
C119 C120 C129 O38 174.4(2) . . . . ?
C121 C120 C129 O38 44.8(3) . . . . ?
C128 C120 C129 O39 115.7(3) . . . . ?
C119 C120 C129 O39 -1.5(3) . . . . ?
C121 C120 C129 O39 -131.2(2) . . . . ?
C127 N126 C130 O40 -166.0(3) . . . . ?
C125 N126 C130 O40 2.8(4) . . . . ?
C127 N126 C130 C131 18.2(4) . . . . ?
C125 N126 C130 C131 -173.0(2) . . . . ?
O40 C130 C131 C132 -115.7(3) . . . . ?
N126 C130 C131 C132 60.2(4) . . . . ?
O40 C130 C131 C136 59.4(4) . . . . ?
N126 C130 C131 C136 -124.7(3) . . . . ?
C136 C131 C132 C133 2.6(5) . . . . ?
C130 C131 C132 C133 177.7(3) . . . . ?
C131 C132 C133 C134 0.6(5) . . . . ?
C132 C133 C134 C135 -2.3(5) . . . . ?
C133 C134 C135 C136 0.9(6) . . . . ?
C134 C135 C136 C131 2.3(6) . . . . ?
C132 C131 C136 C135 -4.0(5) . . . . ?
C130 C131 C136 C135 -179.2(3) . . . . ?
C138 O42 C137 O41 3.3(4) . . . . ?
C138 O42 C137 C128 -178.8(2) . . . . ?
C120 C128 C137 O41 -31.4(4) . . . . ?
C124 C128 C137 O41 -151.2(3) . . . . ?
C116 C128 C137 O41 83.8(4) . . . . ?
C120 C128 C137 O42 150.7(2) . . . . ?
C124 C128 C137 O42 30.9(3) . . . . ?
C116 C128 C137 O42 -94.0(3) . . . . ?

_refine_diff_density_max         0.868
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.094

_shelxl_version_number           2013-4


