# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_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.	2021-09-29 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_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.	2021-09-29 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.	2021-09-29 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


