# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_A2
_database_code_depnum_ccdc_archive 'CCDC 1414396'
_audit_update_record             
;
2015-11-01 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 O8 2-, C12 H14 N2 O 2+, 2(H2 O)'
_chemical_formula_sum            'C30 H30 N2 O11'
_chemical_formula_weight         594.56

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

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

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

_cell_length_a                   13.029(3)
_cell_length_b                   9.107(2)
_cell_length_c                   13.565(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.569(4)
_cell_angle_gamma                90
_cell_volume                     1439.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9491
_exptl_absorpt_correction_T_max  0.9947
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8149
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.678
_diffrn_reflns_theta_max         24.985
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.778
_diffrn_reflns_point_group_measured_fraction_full 0.755
_reflns_number_total             3930
_reflns_number_gt                3354
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.454
_reflns_Friedel_fraction_max     0.522
_reflns_Friedel_fraction_full    0.507

_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-2013 (Sheldrick, 2013)'
_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)+(0.0438P)²+0.2153P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 911 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3930
_refine_ls_number_parameters     428
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.142
_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 0.1797(2) 0.1899(3) -0.11417(19) 0.0234(6) Uani 1 1 d . . . . .
O2 O 0.3348(2) 0.1815(3) 0.11903(19) 0.0253(6) Uani 1 1 d . . . . .
O3 O 0.1452(2) 0.0757(4) -0.2740(2) 0.0349(7) Uani 1 1 d . . . . .
O4 O 0.3969(2) 0.1359(3) -0.0891(2) 0.0286(7) Uani 1 1 d . . . . .
O5 O 0.3502(3) 0.0807(4) 0.2777(2) 0.0390(8) Uani 1 1 d . . . . .
C1 C 0.3746(3) 0.1789(5) 0.2309(3) 0.0265(9) Uani 1 1 d . . . . .
O6 O 0.1237(2) 0.2157(3) 0.1033(2) 0.0330(7) Uani 1 1 d . . . . .
O7 O 0.4018(2) -0.0872(3) -0.0161(2) 0.0311(7) Uani 1 1 d . . . . .
O8 O 0.3693(3) 0.6473(4) 0.0719(3) 0.0376(8) Uani 1 1 d . . . . .
H1 H 0.445(7) 0.630(10) 0.086(6) 0.12(3) Uiso 1 1 d . . . . .
H2 H 0.354(5) 0.724(8) 0.034(5) 0.08(2) Uiso 1 1 d . . . . .
C2 C 0.1316(3) 0.1809(5) -0.2267(3) 0.0265(9) Uani 1 1 d . . . . .
O9 O 0.0628(2) -0.0032(3) 0.0226(2) 0.0346(7) Uani 1 1 d . . . . .
C3 C 0.4470(3) 0.3084(5) 0.2864(3) 0.0262(9) Uani 1 1 d . . . . .
N1 N 0.8238(4) 0.0057(5) 0.8926(3) 0.0349(9) Uani 1 1 d . . . . .
H3 H 0.918(5) 0.025(7) 0.958(4) 0.068(16) Uiso 1 1 d . . . . .
H4 H 0.771(4) 0.048(6) 0.910(4) 0.043(14) Uiso 1 1 d . . . . .
H5 H 0.825(3) -0.087(6) 0.898(3) 0.018(11) Uiso 1 1 d . . . . .
C4 C 0.2516(3) 0.0667(5) 0.0604(3) 0.0244(9) Uani 1 1 d . . . . .
H6 H 0.2823 -0.0292 0.0980 0.029 Uiso 1 1 calc R U . . .
O10 O 0.7648(3) 0.2300(4) 0.4859(2) 0.0396(8) Uani 1 1 d . . . . .
C5 C 0.0631(3) 0.3136(5) -0.2821(3) 0.0255(9) Uani 1 1 d . . . . .
C6 C 0.0448(4) 0.3455(5) -0.3890(3) 0.0302(10) Uani 1 1 d . . . . .
H7 H 0.0780 0.2852 -0.4242 0.036 Uiso 1 1 calc R U . . .
N2 N 0.6304(3) -0.0666(4) 0.0846(3) 0.0282(8) Uani 1 1 d . . . . .
H8 H 0.657(4) -0.026(6) 0.047(4) 0.039(14) Uiso 1 1 d . . . . .
H9 H 0.540(4) -0.066(6) 0.043(4) 0.058(15) Uiso 1 1 d . . . . .
H10 H 0.653(4) -0.173(6) 0.089(4) 0.044(14) Uiso 1 1 d . . . . .
C7 C 0.4473(4) 0.3574(5) 0.3841(3) 0.0315(10) Uani 1 1 d . . . . .
H11 H 0.4022 0.3084 0.4129 0.038 Uiso 1 1 calc R U . . .
C8 C 0.2383(3) 0.0575(4) -0.0560(3) 0.0235(9) Uani 1 1 d . . . . .
H12 H 0.1889 -0.0290 -0.0932 0.028 Uiso 1 1 calc R U . . .
C9 C -0.0225(4) 0.4663(5) -0.4449(3) 0.0353(11) Uani 1 1 d . . . . .
H13 H -0.0326 0.4907 -0.5167 0.042 Uiso 1 1 calc R U . . .
C10 C 0.7763(3) 0.1661(5) 0.5831(3) 0.0302(10) Uani 1 1 d . . . . .
C11 C 0.7364(3) 0.1460(5) 0.3918(3) 0.0291(10) Uani 1 1 d . . . . .
C12 C 0.6696(3) 0.0053(5) 0.1919(3) 0.0263(9) Uani 1 1 d . . . . .
C13 C 0.8539(4) -0.0153(5) 0.7265(4) 0.0336(10) Uani 1 1 d . . . . .
H14 H 0.8965 -0.1027 0.7561 0.040 Uiso 1 1 calc R U . . .
O11 O 0.1127(3) -0.2617(4) -0.0565(3) 0.0445(8) Uani 1 1 d . . . . .
H15 H 0.109(6) -0.190(9) -0.005(6) 0.11(3) Uiso 1 1 d . . . . .
H16 H 0.048(6) -0.299(8) -0.082(5) 0.08(2) Uiso 1 1 d . . . . .
C14 C 0.7424(3) 0.1258(5) 0.2180(3) 0.0289(10) Uani 1 1 d . . . . .
H17 H 0.7692 0.1600 0.1674 0.035 Uiso 1 1 calc R U . . .
C15 C 0.5151(3) 0.3785(5) 0.2458(3) 0.0298(10) Uani 1 1 d . . . . .
H18 H 0.5140 0.3467 0.1786 0.036 Uiso 1 1 calc R U . . .
C16 C 0.6302(4) -0.0459(5) 0.2651(3) 0.0322(10) Uani 1 1 d . . . . .
H19 H 0.5800 -0.1280 0.2463 0.039 Uiso 1 1 calc R U . . .
C17 C 0.5851(4) 0.4959(5) 0.3040(4) 0.0375(11) Uani 1 1 d . . . . .
H20 H 0.6343 0.5413 0.2783 0.045 Uiso 1 1 calc R U . . .
C18 C -0.0745(4) 0.5501(5) -0.3943(4) 0.0353(11) Uani 1 1 d . . . . .
H21 H -0.1220 0.6305 -0.4328 0.042 Uiso 1 1 calc R U . . .
C19 C 0.3550(3) 0.0359(4) -0.0552(3) 0.0241(9) Uani 1 1 d . . . . .
C20 C 0.8385(4) 0.0369(5) 0.6244(4) 0.0347(11) Uani 1 1 d . . . . .
H22 H 0.8698 -0.0147 0.5833 0.042 Uiso 1 1 calc R U . . .
C21 C 0.1369(3) 0.0975(5) 0.0630(3) 0.0260(9) Uani 1 1 d . . . . .
C22 C 0.8068(3) 0.0611(5) 0.7845(3) 0.0283(10) Uani 1 1 d . . . . .
C23 C 0.7460(4) 0.1902(5) 0.7437(3) 0.0340(10) Uani 1 1 d . . . . .
H23 H 0.7151 0.2424 0.7850 0.041 Uiso 1 1 calc R U . . .
C24 C 0.6642(4) 0.0235(5) 0.3659(4) 0.0332(10) Uani 1 1 d . . . . .
H24 H 0.6388 -0.0120 0.4171 0.040 Uiso 1 1 calc R U . . .
C25 C 0.7309(4) 0.2420(5) 0.6425(3) 0.0348(10) Uani 1 1 d . . . . .
H25 H 0.6891 0.3301 0.6136 0.042 Uiso 1 1 calc R U . . .
C26 C 0.5141(4) 0.4786(6) 0.4396(3) 0.0381(11) Uani 1 1 d . . . . .
H26 H 0.5124 0.5145 0.5046 0.046 Uiso 1 1 calc R U . . .
C27 C -0.0579(4) 0.5181(5) -0.2883(3) 0.0335(10) Uani 1 1 d . . . . .
H27 H -0.0939 0.5764 -0.2547 0.040 Uiso 1 1 calc R U . . .
C28 C 0.7757(3) 0.1961(5) 0.3187(3) 0.0306(10) Uani 1 1 d . . . . .
H28 H 0.8255 0.2786 0.3373 0.037 Uiso 1 1 calc R U . . .
C29 C 0.0117(3) 0.4004(5) -0.2308(3) 0.0306(10) Uani 1 1 d . . . . .
H29 H 0.0242 0.3792 -0.1577 0.037 Uiso 1 1 calc R U . . .
C30 C 0.5824(4) 0.5456(5) 0.3993(4) 0.0389(11) Uani 1 1 d . . . . .
H30 H 0.6285 0.6272 0.4376 0.047 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 1.369(4) . ?
O1 C8 1.456(5) . ?
O2 C1 1.367(4) . ?
O2 C4 1.459(5) . ?
O3 C2 1.210(5) . ?
O4 C19 1.250(5) . ?
O5 C1 1.218(5) . ?
C1 C3 1.487(6) . ?
O6 C21 1.254(5) . ?
O7 C19 1.273(5) . ?
O8 H1 0.94(8) . ?
O8 H2 0.84(7) . ?
C2 C5 1.491(6) . ?
O9 C21 1.264(5) . ?
C3 C15 1.392(5) . ?
C3 C7 1.396(6) . ?
N1 C22 1.471(5) . ?
N1 H3 1.16(6) . ?
N1 H4 0.91(5) . ?
N1 H5 0.85(5) . ?
C4 C8 1.512(5) . ?
C4 C21 1.537(5) . ?
C4 H6 1.0000 . ?
O10 C10 1.387(5) . ?
O10 C11 1.389(5) . ?
C5 C6 1.390(6) . ?
C5 C29 1.406(5) . ?
C6 C9 1.400(6) . ?
C6 H7 0.9500 . ?
N2 C12 1.463(5) . ?
N2 H8 0.82(5) . ?
N2 H9 1.05(5) . ?
N2 H10 1.01(5) . ?
C7 C26 1.399(7) . ?
C7 H11 0.9500 . ?
C8 C19 1.528(5) . ?
C8 H12 1.0000 . ?
C9 C18 1.388(6) . ?
C9 H13 0.9500 . ?
C10 C25 1.379(6) . ?
C10 C20 1.396(6) . ?
C11 C28 1.382(5) . ?
C11 C24 1.399(6) . ?
C12 C16 1.388(5) . ?
C12 C14 1.389(6) . ?
C13 C22 1.382(5) . ?
C13 C20 1.392(6) . ?
C13 H14 0.9500 . ?
O11 H15 0.97(8) . ?
O11 H16 0.83(7) . ?
C14 C28 1.391(6) . ?
C14 H17 0.9500 . ?
C15 C17 1.397(6) . ?
C15 H18 0.9500 . ?
C16 C24 1.387(6) . ?
C16 H19 0.9500 . ?
C17 C30 1.386(6) . ?
C17 H20 0.9500 . ?
C18 C27 1.386(6) . ?
C18 H21 0.9500 . ?
C20 H22 0.9500 . ?
C22 C23 1.387(6) . ?
C23 C25 1.381(6) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C30 1.377(6) . ?
C26 H26 0.9500 . ?
C27 C29 1.395(6) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 H30 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
C2 O1 C8 114.9(3) . . ?
C1 O2 C4 114.4(3) . . ?
O5 C1 O2 122.2(4) . . ?
O5 C1 C3 124.9(3) . . ?
O2 C1 C3 112.8(3) . . ?
H1 O8 H2 102(6) . . ?
O3 C2 O1 122.5(4) . . ?
O3 C2 C5 124.8(3) . . ?
O1 C2 C5 112.7(3) . . ?
C15 C3 C7 119.8(4) . . ?
C15 C3 C1 122.4(4) . . ?
C7 C3 C1 117.8(3) . . ?
C22 N1 H3 110(3) . . ?
C22 N1 H4 109(3) . . ?
H3 N1 H4 114(4) . . ?
C22 N1 H5 115(3) . . ?
H3 N1 H5 96(4) . . ?
H4 N1 H5 113(4) . . ?
O2 C4 C8 108.6(3) . . ?
O2 C4 C21 110.4(3) . . ?
C8 C4 C21 112.1(3) . . ?
O2 C4 H6 108.5 . . ?
C8 C4 H6 108.5 . . ?
C21 C4 H6 108.5 . . ?
C10 O10 C11 120.9(3) . . ?
C6 C5 C29 120.1(4) . . ?
C6 C5 C2 118.7(3) . . ?
C29 C5 C2 121.1(3) . . ?
C5 C6 C9 120.2(4) . . ?
C5 C6 H7 119.9 . . ?
C9 C6 H7 119.9 . . ?
C12 N2 H8 111(3) . . ?
C12 N2 H9 110(3) . . ?
H8 N2 H9 110(4) . . ?
C12 N2 H10 114(3) . . ?
H8 N2 H10 106(4) . . ?
H9 N2 H10 105(4) . . ?
C3 C7 C26 120.0(4) . . ?
C3 C7 H11 120.0 . . ?
C26 C7 H11 120.0 . . ?
O1 C8 C4 107.9(3) . . ?
O1 C8 C19 113.0(3) . . ?
C4 C8 C19 110.5(3) . . ?
O1 C8 H12 108.4 . . ?
C4 C8 H12 108.4 . . ?
C19 C8 H12 108.4 . . ?
C18 C9 C6 119.4(4) . . ?
C18 C9 H13 120.3 . . ?
C6 C9 H13 120.3 . . ?
C25 C10 O10 116.9(4) . . ?
C25 C10 C20 120.8(4) . . ?
O10 C10 C20 122.1(4) . . ?
C28 C11 O10 116.4(4) . . ?
C28 C11 C24 120.5(4) . . ?
O10 C11 C24 122.9(4) . . ?
C16 C12 C14 120.8(4) . . ?
C16 C12 N2 119.0(4) . . ?
C14 C12 N2 120.1(3) . . ?
C22 C13 C20 119.4(4) . . ?
C22 C13 H14 120.3 . . ?
C20 C13 H14 120.3 . . ?
H15 O11 H16 102(6) . . ?
C12 C14 C28 119.4(4) . . ?
C12 C14 H17 120.3 . . ?
C28 C14 H17 120.3 . . ?
C3 C15 C17 119.9(4) . . ?
C3 C15 H18 120.1 . . ?
C17 C15 H18 120.1 . . ?
C24 C16 C12 119.7(4) . . ?
C24 C16 H19 120.2 . . ?
C12 C16 H19 120.2 . . ?
C30 C17 C15 119.6(4) . . ?
C30 C17 H20 120.2 . . ?
C15 C17 H20 120.2 . . ?
C27 C18 C9 120.8(4) . . ?
C27 C18 H21 119.6 . . ?
C9 C18 H21 119.6 . . ?
O4 C19 O7 126.0(3) . . ?
O4 C19 C8 120.0(3) . . ?
O7 C19 C8 113.9(3) . . ?
C13 C20 C10 119.1(4) . . ?
C13 C20 H22 120.4 . . ?
C10 C20 H22 120.4 . . ?
O6 C21 O9 125.8(4) . . ?
O6 C21 C4 119.4(3) . . ?
O9 C21 C4 114.8(4) . . ?
C13 C22 C23 121.3(4) . . ?
C13 C22 N1 119.2(4) . . ?
C23 C22 N1 119.5(4) . . ?
C25 C23 C22 119.2(4) . . ?
C25 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C16 C24 C11 119.6(4) . . ?
C16 C24 H24 120.2 . . ?
C11 C24 H24 120.2 . . ?
C10 C25 C23 120.2(4) . . ?
C10 C25 H25 119.9 . . ?
C23 C25 H25 119.9 . . ?
C30 C26 C7 119.5(4) . . ?
C30 C26 H26 120.2 . . ?
C7 C26 H26 120.2 . . ?
C18 C27 C29 120.2(4) . . ?
C18 C27 H27 119.9 . . ?
C29 C27 H27 119.9 . . ?
C11 C28 C14 120.0(4) . . ?
C11 C28 H28 120.0 . . ?
C14 C28 H28 120.0 . . ?
C27 C29 C5 119.3(4) . . ?
C27 C29 H29 120.4 . . ?
C5 C29 H29 120.4 . . ?
C26 C30 C17 121.1(4) . . ?
C26 C30 H30 119.5 . . ?
C17 C30 H30 119.5 . . ?

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 O2 C1 O5 6.3(5) . . . . ?
C4 O2 C1 C3 -172.4(3) . . . . ?
C8 O1 C2 O3 -6.1(5) . . . . ?
C8 O1 C2 C5 174.4(3) . . . . ?
O5 C1 C3 C15 149.7(4) . . . . ?
O2 C1 C3 C15 -31.6(5) . . . . ?
O5 C1 C3 C7 -28.7(6) . . . . ?
O2 C1 C3 C7 149.9(4) . . . . ?
C1 O2 C4 C8 -165.6(3) . . . . ?
C1 O2 C4 C21 71.1(4) . . . . ?
O3 C2 C5 C6 -22.6(6) . . . . ?
O1 C2 C5 C6 156.9(3) . . . . ?
O3 C2 C5 C29 153.5(4) . . . . ?
O1 C2 C5 C29 -27.0(5) . . . . ?
C29 C5 C6 C9 1.6(6) . . . . ?
C2 C5 C6 C9 177.7(4) . . . . ?
C15 C3 C7 C26 1.4(6) . . . . ?
C1 C3 C7 C26 179.9(4) . . . . ?
C2 O1 C8 C4 -161.8(3) . . . . ?
C2 O1 C8 C19 75.7(4) . . . . ?
O2 C4 C8 O1 -69.6(4) . . . . ?
C21 C4 C8 O1 52.7(4) . . . . ?
O2 C4 C8 C19 54.4(4) . . . . ?
C21 C4 C8 C19 176.7(3) . . . . ?
C5 C6 C9 C18 -2.6(6) . . . . ?
C11 O10 C10 C25 -138.4(4) . . . . ?
C11 O10 C10 C20 46.4(5) . . . . ?
C10 O10 C11 C28 -151.5(4) . . . . ?
C10 O10 C11 C24 33.5(6) . . . . ?
C16 C12 C14 C28 -0.2(6) . . . . ?
N2 C12 C14 C28 177.8(4) . . . . ?
C7 C3 C15 C17 1.2(6) . . . . ?
C1 C3 C15 C17 -177.3(4) . . . . ?
C14 C12 C16 C24 -0.4(6) . . . . ?
N2 C12 C16 C24 -178.4(4) . . . . ?
C3 C15 C17 C30 -2.8(7) . . . . ?
C6 C9 C18 C27 1.8(7) . . . . ?
O1 C8 C19 O4 9.0(5) . . . . ?
C4 C8 C19 O4 -112.0(4) . . . . ?
O1 C8 C19 O7 -172.3(3) . . . . ?
C4 C8 C19 O7 66.7(4) . . . . ?
C22 C13 C20 C10 0.5(6) . . . . ?
C25 C10 C20 C13 0.2(6) . . . . ?
O10 C10 C20 C13 175.2(4) . . . . ?
O2 C4 C21 O6 6.1(5) . . . . ?
C8 C4 C21 O6 -115.2(4) . . . . ?
O2 C4 C21 O9 -174.0(3) . . . . ?
C8 C4 C21 O9 64.7(4) . . . . ?
C20 C13 C22 C23 -1.1(6) . . . . ?
C20 C13 C22 N1 -179.8(4) . . . . ?
C13 C22 C23 C25 1.0(6) . . . . ?
N1 C22 C23 C25 179.7(4) . . . . ?
C12 C16 C24 C11 1.2(6) . . . . ?
C28 C11 C24 C16 -1.4(6) . . . . ?
O10 C11 C24 C16 173.3(4) . . . . ?
O10 C10 C25 C23 -175.5(4) . . . . ?
C20 C10 C25 C23 -0.3(7) . . . . ?
C22 C23 C25 C10 -0.3(6) . . . . ?
C3 C7 C26 C30 -2.3(7) . . . . ?
C9 C18 C27 C29 0.0(7) . . . . ?
O10 C11 C28 C14 -174.2(4) . . . . ?
C24 C11 C28 C14 0.9(6) . . . . ?
C12 C14 C28 C11 -0.1(6) . . . . ?
C18 C27 C29 C5 -1.0(6) . . . . ?
C6 C5 C29 C27 0.2(6) . . . . ?
C2 C5 C29 C27 -175.8(4) . . . . ?
C7 C26 C30 C17 0.8(7) . . . . ?
C15 C17 C30 C26 1.8(7) . . . . ?

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.052

_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_B1
_database_code_depnum_ccdc_archive 'CCDC 1414397'
_audit_update_record             
;
2015-11-01 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 O8 2-, C13 H16 N2 2+, 3(H2 O)'
_chemical_formula_sum            'C33 H38 N2 O11'
_chemical_formula_weight         638.65

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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   13.604(2)
_cell_length_b                   9.974(2)
_cell_length_c                   13.840(3)
_cell_angle_alpha                90
_cell_angle_beta                 119.099(4)
_cell_angle_gamma                90
_cell_volume                     1640.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       platelet
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             676
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9846
_exptl_absorpt_correction_T_max  0.9981
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'

_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 SMART APEX2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3416
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.684
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.906
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.906
_diffrn_reflns_point_group_measured_fraction_max 0.678
_diffrn_reflns_point_group_measured_fraction_full 0.658
_reflns_number_total             1956
_reflns_number_gt                1845
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.368
_reflns_Friedel_fraction_max     0.390
_reflns_Friedel_fraction_full    0.378

_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-2013 (Sheldrick, 2013)'
_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)+(0.0715P)²+0.4055P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 474 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   1.1(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         1956
_refine_ls_number_parameters     234
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0972
_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
O1 O 0.96246(17) 0.9071(2) 0.88587(17) 0.0194(5) Uani 1 1 d . . . . .
O2 O 1.0000 0.5231(3) 1.0000 0.0219(7) Uani 1 2 d S T P . .
H1 H 1.019(3) 0.477(5) 0.960(3) 0.038(12) Uiso 1 1 d . . . . .
O3 O 0.81871(16) 1.1225(2) 0.98344(18) 0.0222(5) Uani 1 1 d . . . . .
O4 O 0.84151(19) 1.0035(2) 0.72433(18) 0.0274(6) Uani 1 1 d . . . . .
O5 O 0.77572(17) 0.9199(2) 0.90547(17) 0.0228(5) Uani 1 1 d . . . . .
O6 O 0.5786(2) 0.8551(3) 0.9056(2) 0.0266(6) Uani 1 1 d . . . . .
H2 H 0.603(4) 0.795(5) 0.951(4) 0.039(13) Uiso 1 1 d . . . . .
H3 H 0.633(5) 0.887(7) 0.898(5) 0.078(19) Uiso 1 1 d . . . . .
C1 C 0.5775(3) 0.4394(3) 0.6012(3) 0.0232(7) Uani 1 1 d . . . . .
N1 N 0.7922(2) 0.6458(3) 0.8978(2) 0.0206(6) Uani 1 1 d . . . . .
H4 H 0.789(3) 0.733(5) 0.886(3) 0.033(10) Uiso 1 1 d . . . . .
H5 H 0.862(4) 0.614(4) 0.926(3) 0.033(10) Uiso 1 1 d . . . . .
H6 H 0.763(4) 0.629(5) 0.952(4) 0.046(12) Uiso 1 1 d . . . . .
C2 C 0.8999(2) 0.9100(3) 0.7739(3) 0.0200(7) Uani 1 1 d . . . . .
C3 C 1.0247(3) 0.7266(3) 0.7736(3) 0.0245(7) Uani 1 1 d . . . . .
H7 H 1.0835 0.7635 0.8399 0.029 Uiso 1 1 calc R U . . .
C4 C 0.9171(3) 0.7858(3) 0.7239(3) 0.0213(7) Uani 1 1 d . . . . .
C5 C 0.9501(2) 1.0221(3) 0.9416(2) 0.0179(6) Uani 1 1 d . . . . .
H8 H 0.9533 1.1050 0.9026 0.021 Uiso 1 1 calc R U . . .
C6 C 0.7188(3) 0.5761(3) 0.7945(2) 0.0204(7) Uani 1 1 d . . . . .
C7 C 0.5000 0.3588(5) 0.5000 0.0250(10) Uani 1 2 d S T P . .
H9 H 0.4534 0.3001 0.5192 0.030 Uiso 0.5 1 calc R U P . .
H10 H 0.5466 0.3001 0.4808 0.030 Uiso 0.5 1 calc R U P . .
C8 C 1.0454(3) 0.6157(4) 0.7268(3) 0.0302(8) Uani 1 1 d . . . . .
H11 H 1.1185 0.5773 0.7598 0.036 Uiso 1 1 calc R U . . .
C9 C 0.8297(3) 0.7302(4) 0.6279(3) 0.0241(7) Uani 1 1 d . . . . .
C10 C 0.7622(3) 0.4779(3) 0.7559(3) 0.0249(8) Uani 1 1 d . . . . .
H12 H 0.8401 0.4569 0.7953 0.030 Uiso 1 1 calc R U . . .
C11 C 0.8525(3) 0.6164(4) 0.5839(3) 0.0280(8) Uani 1 1 d . . . . .
H13 H 0.7935 0.5763 0.5195 0.034 Uiso 1 1 calc R U . . .
C12 C 0.6916(3) 0.4100(4) 0.6593(3) 0.0268(8) Uani 1 1 d . . . . .
H14 H 0.7216 0.3426 0.6325 0.032 Uiso 1 1 calc R U . . .
C13 C 0.8380(2) 1.0199(3) 0.9431(2) 0.0181(7) Uani 1 1 d . . . . .
C14 C 0.5360(3) 0.5398(3) 0.6411(3) 0.0241(7) Uani 1 1 d . . . . .
H15 H 0.4584 0.5620 0.6014 0.029 Uiso 1 1 calc R U . . .
C15 C 0.7110(3) 0.7848(4) 0.5721(3) 0.0302(8) Uani 1 1 d . . . . .
H16 H 0.6981 0.8382 0.5076 0.045 Uiso 1 1 calc R U . . .
H17 H 0.7004 0.8413 0.6243 0.045 Uiso 1 1 calc R U . . .
H18 H 0.6574 0.7101 0.5484 0.045 Uiso 1 1 calc R U . . .
C16 C 0.6056(3) 0.6082(3) 0.7374(3) 0.0237(7) Uani 1 1 d . . . . .
H19 H 0.5761 0.6762 0.7641 0.028 Uiso 1 1 calc R U . . .
C17 C 0.9588(3) 0.5604(4) 0.6314(3) 0.0306(8) Uani 1 1 d . . . . .
H20 H 0.9726 0.4840 0.5987 0.037 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 1.358(4) . ?
O1 C5 1.436(4) . ?
O2 H1 0.85(4) . ?
O3 C13 1.253(4) . ?
O4 C2 1.201(4) . ?
O5 C13 1.247(4) . ?
O6 H2 0.82(5) . ?
O6 H3 0.86(7) . ?
C1 C14 1.389(5) . ?
C1 C12 1.389(5) . ?
C1 C7 1.511(4) . ?
N1 C6 1.462(4) . ?
N1 H4 0.89(5) . ?
N1 H5 0.89(4) . ?
N1 H6 1.02(5) . ?
C2 C4 1.491(5) . ?
C3 C8 1.378(5) . ?
C3 C4 1.409(5) . ?
C3 H7 0.9500 . ?
C4 C9 1.397(5) . ?
C5 C5 1.524(6) 2_757 ?
C5 C13 1.536(4) . ?
C5 H8 1.0000 . ?
C6 C10 1.379(5) . ?
C6 C16 1.383(5) . ?
C7 C1 1.511(4) 2_656 ?
C7 H9 0.9900 . ?
C7 H10 0.9900 . ?
C8 C17 1.386(5) . ?
C8 H11 0.9500 . ?
C9 C11 1.393(5) . ?
C9 C15 1.513(5) . ?
C10 C12 1.386(5) . ?
C10 H12 0.9500 . ?
C11 C17 1.383(5) . ?
C11 H13 0.9500 . ?
C12 H14 0.9500 . ?
C14 C16 1.382(5) . ?
C14 H15 0.9500 . ?
C15 H16 0.9800 . ?
C15 H17 0.9800 . ?
C15 H18 0.9800 . ?
C16 H19 0.9500 . ?
C17 H20 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
C2 O1 C5 115.1(2) . . ?
H2 O6 H3 109(5) . . ?
C14 C1 C12 118.5(3) . . ?
C14 C1 C7 121.2(3) . . ?
C12 C1 C7 120.2(3) . . ?
C6 N1 H4 110(3) . . ?
C6 N1 H5 109(3) . . ?
H4 N1 H5 112(4) . . ?
C6 N1 H6 109(2) . . ?
H4 N1 H6 107(4) . . ?
H5 N1 H6 110(4) . . ?
O4 C2 O1 122.8(3) . . ?
O4 C2 C4 126.2(3) . . ?
O1 C2 C4 111.0(3) . . ?
C8 C3 C4 120.5(3) . . ?
C8 C3 H7 119.7 . . ?
C4 C3 H7 119.7 . . ?
C9 C4 C3 120.0(3) . . ?
C9 C4 C2 121.2(3) . . ?
C3 C4 C2 118.8(3) . . ?
O1 C5 C5 107.1(2) . 2_757 ?
O1 C5 C13 111.8(2) . . ?
C5 C5 C13 111.3(3) 2_757 . ?
O1 C5 H8 108.9 . . ?
C5 C5 H8 108.9 2_757 . ?
C13 C5 H8 108.9 . . ?
C10 C6 C16 120.7(3) . . ?
C10 C6 N1 119.9(3) . . ?
C16 C6 N1 119.3(3) . . ?
C1 C7 C1 115.7(4) . 2_656 ?
C1 C7 H9 108.4 . . ?
C1 C7 H9 108.4 2_656 . ?
C1 C7 H10 108.4 . . ?
C1 C7 H10 108.4 2_656 . ?
H9 C7 H10 107.4 . . ?
C3 C8 C17 119.6(3) . . ?
C3 C8 H11 120.2 . . ?
C17 C8 H11 120.2 . . ?
C11 C9 C4 118.2(3) . . ?
C11 C9 C15 118.7(3) . . ?
C4 C9 C15 123.1(3) . . ?
C6 C10 C12 119.6(3) . . ?
C6 C10 H12 120.2 . . ?
C12 C10 H12 120.2 . . ?
C17 C11 C9 121.7(3) . . ?
C17 C11 H13 119.2 . . ?
C9 C11 H13 119.2 . . ?
C10 C12 C1 120.7(3) . . ?
C10 C12 H14 119.6 . . ?
C1 C12 H14 119.6 . . ?
O5 C13 O3 126.3(3) . . ?
O5 C13 C5 118.9(3) . . ?
O3 C13 C5 114.8(3) . . ?
C16 C14 C1 121.3(3) . . ?
C16 C14 H15 119.4 . . ?
C1 C14 H15 119.4 . . ?
C9 C15 H16 109.5 . . ?
C9 C15 H17 109.5 . . ?
H16 C15 H17 109.5 . . ?
C9 C15 H18 109.5 . . ?
H16 C15 H18 109.5 . . ?
H17 C15 H18 109.5 . . ?
C14 C16 C6 119.1(3) . . ?
C14 C16 H19 120.4 . . ?
C6 C16 H19 120.4 . . ?
C11 C17 C8 120.0(3) . . ?
C11 C17 H20 120.0 . . ?
C8 C17 H20 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
C5 O1 C2 O4 2.5(4) . . . . ?
C5 O1 C2 C4 -179.1(2) . . . . ?
C8 C3 C4 C9 1.5(5) . . . . ?
C8 C3 C4 C2 -176.8(3) . . . . ?
O4 C2 C4 C9 -35.7(5) . . . . ?
O1 C2 C4 C9 146.0(3) . . . . ?
O4 C2 C4 C3 142.6(3) . . . . ?
O1 C2 C4 C3 -35.7(4) . . . . ?
C2 O1 C5 C5 -162.8(3) . . . 2_757 ?
C2 O1 C5 C13 75.0(3) . . . . ?
C14 C1 C7 C1 52.0(3) . . . 2_656 ?
C12 C1 C7 C1 -130.9(4) . . . 2_656 ?
C4 C3 C8 C17 -1.4(5) . . . . ?
C3 C4 C9 C11 -0.2(5) . . . . ?
C2 C4 C9 C11 178.1(3) . . . . ?
C3 C4 C9 C15 177.7(3) . . . . ?
C2 C4 C9 C15 -4.0(5) . . . . ?
C16 C6 C10 C12 -0.4(5) . . . . ?
N1 C6 C10 C12 178.4(3) . . . . ?
C4 C9 C11 C17 -1.3(5) . . . . ?
C15 C9 C11 C17 -179.3(3) . . . . ?
C6 C10 C12 C1 -0.3(5) . . . . ?
C14 C1 C12 C10 1.0(5) . . . . ?
C7 C1 C12 C10 -176.1(3) . . . . ?
O1 C5 C13 O5 5.0(4) . . . . ?
C5 C5 C13 O5 -114.7(2) 2_757 . . . ?
O1 C5 C13 O3 -175.0(2) . . . . ?
C5 C5 C13 O3 65.3(3) 2_757 . . . ?
C12 C1 C14 C16 -1.1(5) . . . . ?
C7 C1 C14 C16 176.0(3) . . . . ?
C1 C14 C16 C6 0.4(5) . . . . ?
C10 C6 C16 C14 0.3(5) . . . . ?
N1 C6 C16 C14 -178.5(3) . . . . ?
C9 C11 C17 C8 1.5(6) . . . . ?
C3 C8 C17 C11 -0.1(6) . . . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.044

_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_B2
_database_code_depnum_ccdc_archive 'CCDC 1414398'
_audit_update_record             
;
2015-11-01 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C20 H16 O8 2-, C12 H14 N2 O 2+, 3(H2 O)
;
_chemical_formula_sum            'C32 H36 N2 O12'
_chemical_formula_weight         640.63

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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   13.524(2)
_cell_length_b                   9.9285(16)
_cell_length_c                   13.891(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.8166(19)
_cell_angle_gamma                90
_cell_volume                     1634.2(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       platelet
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             676
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3938
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.673
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.898
_reflns_number_total             2652
_reflns_number_gt                2595
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_max     0.837
_reflns_Friedel_fraction_full    0.815

_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-2013 (Sheldrick, 2013)'
_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)+(0.0506P)²+0.4864P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1090 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   1.2(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2652
_refine_ls_number_parameters     234
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0777
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.5000 0.5026(3) 0.0000 0.0341(5) Uani 1 2 d S T P . .
O2 O 0.72401(12) 0.10385(17) 0.09280(12) 0.0332(4) Uani 1 1 d . . . . .
O3 O 0.53727(11) 0.11046(16) 0.11441(11) 0.0275(3) Uani 1 1 d . . . . .
O4 O 0.65777(14) 0.01089(19) 0.27396(13) 0.0401(4) Uani 1 1 d . . . . .
O5 O 0.68138(13) -0.09723(16) 0.01042(13) 0.0336(4) Uani 1 1 d . . . . .
N1 N 0.70749(16) 0.3790(2) 0.10830(15) 0.0286(4) Uani 1 1 d . . . . .
O6 O 1.0000 0.6434(2) 0.5000 0.0456(6) Uani 1 2 d S T P . .
O7 O 0.92344(15) 0.16972(19) 0.09674(15) 0.0392(4) Uani 1 1 d . . . . .
C2 C 0.9277(2) 0.5704(2) 0.40661(18) 0.0362(5) Uani 1 1 d . . . . .
C3 C 0.78265(19) 0.4437(2) 0.21330(17) 0.0287(5) Uani 1 1 d . . . . .
C4 C 0.66196(16) 0.0033(2) 0.05377(16) 0.0263(4) Uani 1 1 d . . . . .
C17 C 0.59758(17) 0.1048(2) 0.22612(16) 0.0289(4) Uani 1 1 d . . . . .
C5 C 0.5764(2) 0.2255(2) 0.27635(17) 0.0314(5) Uani 1 1 d . . . . .
C6 C 0.55033(16) -0.0036(2) 0.05762(16) 0.0253(4) Uani 1 1 d . . . . .
H1 H 0.5491 -0.0880 0.0963 0.030 Uiso 1 1 calc R U . . .
C7 C 0.4702(2) 0.2870(3) 0.22374(19) 0.0396(6) Uani 1 1 d . . . . .
H2 H 0.4145 0.2549 0.1541 0.048 Uiso 1 1 calc R U . . .
C8 C 0.8933(2) 0.4005(3) 0.27201(18) 0.0368(5) Uani 1 1 d . . . . .
H3 H 0.9192 0.3276 0.2458 0.044 Uiso 1 1 calc R U . . .
C9 C 0.7444(2) 0.5502(3) 0.2505(2) 0.0397(6) Uani 1 1 d . . . . .
H4 H 0.6684 0.5796 0.2094 0.048 Uiso 1 1 calc R U . . .
C10 C 0.6599(2) 0.2738(3) 0.37831(19) 0.0404(6) Uani 1 1 d . . . . .
C11 C 0.9660(2) 0.4644(3) 0.36944(19) 0.0411(6) Uani 1 1 d . . . . .
H5 H 1.0421 0.4353 0.4106 0.049 Uiso 1 1 calc R U . . .
C12 C 0.8174(2) 0.6141(3) 0.3480(2) 0.0427(6) Uani 1 1 d . . . . .
H6 H 0.7918 0.6873 0.3741 0.051 Uiso 1 1 calc R U . . .
C13 C 0.6333(3) 0.3830(3) 0.4245(2) 0.0522(7) Uani 1 1 d . . . . .
H7 H 0.6889 0.4179 0.4931 0.063 Uiso 1 1 calc R U . . .
C14 C 0.4458(3) 0.3936(3) 0.2721(2) 0.0518(7) Uani 1 1 d . . . . .
H8 H 0.3732 0.4341 0.2367 0.062 Uiso 1 1 calc R U . . .
C15 C 0.7770(2) 0.2160(3) 0.4380(2) 0.0565(8) Uani 1 1 d . . . . .
H9 H 0.8271 0.2796 0.4944 0.085 Uiso 1 1 calc R U . . .
H10 H 0.8049 0.1998 0.3857 0.085 Uiso 1 1 calc R U . . .
H11 H 0.7754 0.1308 0.4729 0.085 Uiso 1 1 calc R U . . .
C16 C 0.5283(3) 0.4411(3) 0.3728(2) 0.0572(8) Uani 1 1 d . . . . .
H12 H 0.5119 0.5149 0.4064 0.069 Uiso 1 1 calc R U . . .
H14 H 0.735(2) 0.394(3) 0.058(2) 0.041(7) Uiso 1 1 d . . . . .
H13 H 0.707(2) 0.293(3) 0.116(2) 0.031(7) Uiso 1 1 d . . . . .
H15 H 0.636(3) 0.415(3) 0.079(2) 0.041(7) Uiso 1 1 d . . . . .
H16 H 0.478(3) 0.564(4) 0.038(2) 0.058(9) Uiso 1 1 d . . . . .
H17 H 0.865(3) 0.134(4) 0.100(3) 0.082(12) Uiso 1 1 d . . . . .
H18 H 0.894(3) 0.245(4) 0.052(3) 0.059(9) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H16 0.94(3) . ?
O2 C4 1.248(3) . ?
O3 C17 1.363(2) . ?
O3 C6 1.439(3) . ?
O4 C17 1.205(3) . ?
O5 C4 1.257(3) . ?
N1 C3 1.464(3) . ?
N1 H14 0.94(3) . ?
N1 H13 0.86(3) . ?
N1 H15 0.92(3) . ?
O6 C2 1.393(3) . ?
O6 C2 1.393(3) 2_756 ?
O7 H17 0.89(4) . ?
O7 H18 0.93(4) . ?
C2 C11 1.379(4) . ?
C2 C12 1.380(4) . ?
C3 C9 1.382(3) . ?
C3 C8 1.383(3) . ?
C4 C6 1.538(3) . ?
C17 C5 1.482(3) . ?
C5 C7 1.399(3) . ?
C5 C10 1.403(3) . ?
C6 C6 1.521(4) 2_655 ?
C6 H1 1.0000 . ?
C7 C14 1.376(4) . ?
C7 H2 0.9500 . ?
C8 C11 1.385(4) . ?
C8 H3 0.9500 . ?
C9 C12 1.386(4) . ?
C9 H4 0.9500 . ?
C10 C13 1.392(4) . ?
C10 C15 1.504(4) . ?
C11 H5 0.9500 . ?
C12 H6 0.9500 . ?
C13 C16 1.372(5) . ?
C13 H7 0.9500 . ?
C14 C16 1.386(5) . ?
C14 H8 0.9500 . ?
C15 H9 0.9800 . ?
C15 H10 0.9800 . ?
C15 H11 0.9800 . ?
C16 H12 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
C17 O3 C6 115.33(16) . . ?
C3 N1 H14 109.4(17) . . ?
C3 N1 H13 110.8(16) . . ?
H14 N1 H13 107(3) . . ?
C3 N1 H15 110.4(18) . . ?
H14 N1 H15 108(2) . . ?
H13 N1 H15 112(3) . . ?
C2 O6 C2 117.4(3) . 2_756 ?
H17 O7 H18 105(3) . . ?
C11 C2 C12 120.9(2) . . ?
C11 C2 O6 121.6(2) . . ?
C12 C2 O6 117.4(2) . . ?
C9 C3 C8 120.7(2) . . ?
C9 C3 N1 120.2(2) . . ?
C8 C3 N1 119.0(2) . . ?
O2 C4 O5 126.26(18) . . ?
O2 C4 C6 119.10(19) . . ?
O5 C4 C6 114.63(18) . . ?
O4 C17 O3 122.3(2) . . ?
O4 C17 C5 126.75(19) . . ?
O3 C17 C5 110.96(18) . . ?
C7 C5 C10 120.1(2) . . ?
C7 C5 C17 119.30(19) . . ?
C10 C5 C17 120.5(2) . . ?
O3 C6 C6 107.03(13) . 2_655 ?
O3 C6 C4 111.47(17) . . ?
C6 C6 C4 111.03(19) 2_655 . ?
O3 C6 H1 109.1 . . ?
C6 C6 H1 109.1 2_655 . ?
C4 C6 H1 109.1 . . ?
C14 C7 C5 120.5(2) . . ?
C14 C7 H2 119.7 . . ?
C5 C7 H2 119.7 . . ?
C3 C8 C11 119.4(2) . . ?
C3 C8 H3 120.3 . . ?
C11 C8 H3 120.3 . . ?
C3 C9 C12 119.8(2) . . ?
C3 C9 H4 120.1 . . ?
C12 C9 H4 120.1 . . ?
C13 C10 C5 118.1(2) . . ?
C13 C10 C15 118.7(2) . . ?
C5 C10 C15 123.2(3) . . ?
C2 C11 C8 119.9(2) . . ?
C2 C11 H5 120.1 . . ?
C8 C11 H5 120.1 . . ?
C2 C12 C9 119.4(2) . . ?
C2 C12 H6 120.3 . . ?
C9 C12 H6 120.3 . . ?
C16 C13 C10 121.2(2) . . ?
C16 C13 H7 119.4 . . ?
C10 C13 H7 119.4 . . ?
C7 C14 C16 119.3(3) . . ?
C7 C14 H8 120.4 . . ?
C16 C14 H8 120.4 . . ?
C10 C15 H9 109.5 . . ?
C10 C15 H10 109.5 . . ?
H9 C15 H10 109.5 . . ?
C10 C15 H11 109.5 . . ?
H9 C15 H11 109.5 . . ?
H10 C15 H11 109.5 . . ?
C13 C16 C14 120.8(3) . . ?
C13 C16 H12 119.6 . . ?
C14 C16 H12 119.6 . . ?

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
C2 O6 C2 C11 -47.56(19) 2_756 . . . ?
C2 O6 C2 C12 136.9(3) 2_756 . . . ?
C6 O3 C17 O4 0.1(3) . . . . ?
C6 O3 C17 C5 -178.88(16) . . . . ?
O4 C17 C5 C7 -146.6(2) . . . . ?
O3 C17 C5 C7 32.3(3) . . . . ?
O4 C17 C5 C10 30.2(3) . . . . ?
O3 C17 C5 C10 -150.9(2) . . . . ?
C17 O3 C6 C6 160.35(16) . . . 2_655 ?
C17 O3 C6 C4 -78.1(2) . . . . ?
O2 C4 C6 O3 -3.4(2) . . . . ?
O5 C4 C6 O3 176.33(17) . . . . ?
O2 C4 C6 C6 115.87(16) . . . 2_655 ?
O5 C4 C6 C6 -64.43(18) . . . 2_655 ?
C10 C5 C7 C14 -1.1(4) . . . . ?
C17 C5 C7 C14 175.7(2) . . . . ?
C9 C3 C8 C11 0.4(4) . . . . ?
N1 C3 C8 C11 177.7(2) . . . . ?
C8 C3 C9 C12 -0.4(4) . . . . ?
N1 C3 C9 C12 -177.6(2) . . . . ?
C7 C5 C10 C13 0.2(4) . . . . ?
C17 C5 C10 C13 -176.6(2) . . . . ?
C7 C5 C10 C15 -177.9(2) . . . . ?
C17 C5 C10 C15 5.3(4) . . . . ?
C12 C2 C11 C8 0.0(4) . . . . ?
O6 C2 C11 C8 -175.4(2) . . . . ?
C3 C8 C11 C2 -0.2(4) . . . . ?
C11 C2 C12 C9 0.1(4) . . . . ?
O6 C2 C12 C9 175.7(2) . . . . ?
C3 C9 C12 C2 0.1(4) . . . . ?
C5 C10 C13 C16 0.7(4) . . . . ?
C15 C10 C13 C16 179.0(3) . . . . ?
C5 C7 C14 C16 1.1(4) . . . . ?
C10 C13 C16 C14 -0.8(5) . . . . ?
C7 C14 C16 C13 -0.1(5) . . . . ?

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.034

_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_C1
_database_code_depnum_ccdc_archive 'CCDC 1414399'
_audit_update_record             
;
2015-11-01 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C20 H17 O8 1-, 0.5(C13 H16 N2 2+), 0.5(C4 H10 O)
;
_chemical_formula_sum            'C28.50 H30 N O8.50'
_chemical_formula_weight         522.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   16.286(7)
_cell_length_b                   22.708(9)
_cell_length_c                   7.950(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.707(5)
_cell_angle_gamma                90
_cell_volume                     2649.2(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6331
_diffrn_reflns_av_unetI/netI     0.0843
_diffrn_reflns_av_R_equivalents  0.1178
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         1.652
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.898
_reflns_number_total             4317
_reflns_number_gt                3460
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_max     0.846
_reflns_Friedel_fraction_full    0.823

_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-2013 (Sheldrick, 2013)'
_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)+(0.1202P)²+0.1993P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1323 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -1.3(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4317
_refine_ls_number_parameters     349
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1885
_refine_ls_wR_factor_gt          0.1704
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.0892(2) 0.35928(15) 0.1357(5) 0.0323(8) Uani 1 1 d . . . . .
O2 O 0.4103(2) 0.58240(17) -0.0263(5) 0.0364(9) Uani 1 1 d . . . . .
O3 O -0.0839(3) 0.27763(19) 0.1819(5) 0.0424(10) Uani 1 1 d . . . . .
N1 N 0.3266(3) 0.7374(2) 0.3880(7) 0.0328(10) Uani 1 1 d . . . . .
O4 O 0.4616(3) 0.61675(19) 0.3273(5) 0.0463(11) Uani 1 1 d . . . . .
H1 H 0.4782 0.6312 0.4344 0.069 Uiso 0.5 1 calc R U P . .
O5 O 0.2065(3) 0.31083(17) 0.3575(6) 0.0403(9) Uani 1 1 d . . . . .
O6 O 0.0321(3) 0.32978(17) 0.3883(5) 0.0368(9) Uani 1 1 d . . . . .
H36 H 0.0108 0.3193 0.4628 0.055 Uiso 0.5 1 calc R U P . .
C1 C 0.4626(4) 0.6352(2) 0.0334(7) 0.0319(11) Uani 1 1 d . . . . .
H2 H 0.4213 0.6694 -0.0251 0.038 Uiso 1 1 calc R U . . .
O7 O 0.5705(3) 0.6733(2) 0.3200(5) 0.0495(11) Uani 1 1 d . . . . .
C2 C 0.0340(3) 0.3073(2) 0.1009(7) 0.0295(11) Uani 1 1 d . . . . .
H3 H 0.0742 0.2720 0.1243 0.035 Uiso 1 1 calc R U . . .
C3 C 0.5031(4) 0.6421(2) 0.2463(7) 0.0310(12) Uani 1 1 d . . . . .
C4 C 0.3094(4) 0.4157(3) 0.4609(8) 0.0393(13) Uani 1 1 d . . . . .
H4 H 0.3346 0.3814 0.5337 0.047 Uiso 1 1 calc R U . . .
C5 C 0.1747(4) 0.3562(2) 0.2740(7) 0.0322(12) Uani 1 1 d . . . . .
C6 C 0.1868(4) 0.4625(3) 0.2025(9) 0.0405(13) Uani 1 1 d . . . . .
H5 H 0.1282 0.4615 0.0997 0.049 Uiso 1 1 calc R U . . .
O8 O 0.2815(3) 0.6352(3) -0.1654(7) 0.0698(15) Uani 1 1 d . . . . .
C7 C 0.3217(4) 0.5162(3) 0.3979(10) 0.0493(16) Uani 1 1 d . . . . .
H6 H 0.3548 0.5521 0.4273 0.059 Uiso 1 1 calc R U . . .
C8 C 0.2228(4) 0.4128(3) 0.3094(8) 0.0353(12) Uani 1 1 d . . . . .
C9 C 0.2409(3) 0.7045(2) 0.2836(8) 0.0360(13) Uani 1 1 d . . . . .
C10 C 0.3585(4) 0.4675(3) 0.5059(9) 0.0436(14) Uani 1 1 d . . . . .
C11 C 0.2380(5) 0.5138(3) 0.2483(11) 0.0518(16) Uani 1 1 d . . . . .
H7 H 0.2144 0.5480 0.1742 0.062 Uiso 1 1 calc R U . . .
C12 C 0.2728(4) 0.5293(5) -0.1694(9) 0.064(2) Uani 1 1 d . . . . .
C13 C -0.0119(4) 0.3048(2) 0.2322(7) 0.0316(11) Uani 1 1 d . . . . .
C14 C 0.3184(4) 0.5884(3) -0.1231(8) 0.0465(15) Uani 1 1 d . . . . .
C15 C 0.4514(5) 0.4693(3) 0.6720(10) 0.0577(18) Uani 1 1 d . . . . .
H8 H 0.4670 0.4300 0.7279 0.087 Uiso 1 1 calc R U . . .
H9 H 0.4501 0.4972 0.7649 0.087 Uiso 1 1 calc R U . . .
H10 H 0.4973 0.4819 0.6307 0.087 Uiso 1 1 calc R U . . .
C16 C 0.2089(5) 0.6970(3) 0.0992(10) 0.0515(16) Uani 1 1 d . . . . .
H11 H 0.2386 0.7146 0.0319 0.062 Uiso 1 1 calc R U . . .
C17 C 0.0856(4) 0.6390(3) 0.1017(12) 0.062(2) Uani 1 1 d . . . . .
C18 C 0.3157(5) 0.4783(4) -0.0807(11) 0.061(2) Uani 1 1 d . . . . .
H12 H 0.3770 0.4796 0.0121 0.073 Uiso 1 1 calc R U . . .
C19 C 0.2689(7) 0.4241(5) -0.1272(13) 0.085(3) Uani 1 1 d . . . . .
C20 C 0.1992(5) 0.6806(4) 0.3851(11) 0.063(2) Uani 1 1 d . . . . .
H13 H 0.2228 0.6863 0.5161 0.075 Uiso 1 1 calc R U . . .
C21 C 0.1394(8) 0.4711(8) -0.3483(19) 0.119(4) Uani 1 1 d . . . . .
H14 H 0.0780 0.4683 -0.4399 0.142 Uiso 1 1 calc R U . . .
C22 C 0.1298(5) 0.6624(3) 0.0070(11) 0.065(2) Uani 1 1 d . . . . .
H15 H 0.1073 0.6554 -0.1233 0.079 Uiso 1 1 calc R U . . .
C23 C 0.1841(9) 0.4216(6) -0.2581(18) 0.106(4) Uani 1 1 d . . . . .
H16 H 0.1539 0.3847 -0.2898 0.128 Uiso 1 1 calc R U . . .
C24 C 0.1197(5) 0.6472(4) 0.2857(14) 0.076(2) Uani 1 1 d . . . . .
H17 H 0.0894 0.6299 0.3521 0.091 Uiso 1 1 calc R U . . .
C25 C 0.0000 0.6015(5) 0.0000 0.094(5) Uani 1 2 d S T P . .
H18 H -0.0087 0.5759 0.0916 0.113 Uiso 0.5 1 calc R U P . .
H19 H 0.0087 0.5759 -0.0916 0.113 Uiso 0.5 1 calc R U P . .
C26 C 0.1840(6) 0.5272(6) -0.3065(15) 0.099(3) Uani 1 1 d . . . . .
H20 H 0.1536 0.5618 -0.3708 0.119 Uiso 1 1 calc R U . . .
C27 C 0.3138(10) 0.3697(5) -0.033(2) 0.124(5) Uani 1 1 d . . . . .
H21 H 0.2676 0.3401 -0.0465 0.186 Uiso 1 1 calc R U . . .
H22 H 0.3510 0.3778 0.1000 0.186 Uiso 1 1 calc R U . . .
H23 H 0.3529 0.3550 -0.0888 0.186 Uiso 1 1 calc R U . . .
O9 O -0.0253(18) 0.7882(12) 0.727(4) 0.177(9) Uiso 0.5 1 d . . P . .
C28 C -0.111(3) 0.7619(18) 0.332(6) 0.318(17) Uiso 1 1 d . . . . .
C29 C -0.024(4) 0.7839(19) 0.554(9) 0.38(3) Uiso 1 1 d . . . . .
H38 H 0.315(4) 0.763(3) 0.452(8) 0.027(15) Uiso 1 1 d . . . . .
H39 H 0.354(4) 0.753(3) 0.314(9) 0.044(17) Uiso 1 1 d . . . . .
H37 H 0.373(6) 0.709(4) 0.491(11) 0.07(2) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.351(6) . ?
O1 C2 1.437(6) . ?
O2 C14 1.360(7) . ?
O2 C1 1.428(6) . ?
O3 C13 1.227(7) . ?
N1 C9 1.479(7) . ?
O4 C3 1.256(7) . ?
O5 C5 1.212(7) . ?
O6 C13 1.266(7) . ?
C1 C1 1.527(11) 2_655 ?
C1 C3 1.535(7) . ?
O7 C3 1.222(7) . ?
C2 C2 1.503(10) 2 ?
C2 C13 1.527(7) . ?
C4 C10 1.379(9) . ?
C4 C8 1.404(8) . ?
C5 C8 1.468(8) . ?
C6 C8 1.381(8) . ?
C6 C11 1.387(9) . ?
O8 C14 1.193(8) . ?
C7 C11 1.368(10) . ?
C7 C10 1.369(9) . ?
C9 C16 1.337(9) . ?
C9 C20 1.372(10) . ?
C10 C15 1.518(9) . ?
C12 C18 1.379(12) . ?
C12 C26 1.384(11) . ?
C12 C14 1.501(11) . ?
C16 C22 1.412(10) . ?
C17 C24 1.333(13) . ?
C17 C22 1.356(13) . ?
C17 C25 1.532(9) . ?
C18 C19 1.410(11) . ?
C19 C23 1.321(16) . ?
C19 C27 1.465(18) . ?
C20 C24 1.410(11) . ?
C21 C23 1.361(18) . ?
C21 C26 1.433(18) . ?
C25 C17 1.532(9) 2 ?
O9 C29 1.39(6) . ?
C28 C29 1.79(6) . ?
C29 C29 1.40(11) 2_556 ?

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 C2 116.8(4) . . ?
C14 O2 C1 117.0(5) . . ?
O2 C1 C1 109.6(3) . 2_655 ?
O2 C1 C3 111.2(4) . . ?
C1 C1 C3 111.0(5) 2_655 . ?
O1 C2 C2 108.4(3) . 2 ?
O1 C2 C13 110.5(4) . . ?
C2 C2 C13 112.1(5) 2 . ?
O7 C3 O4 126.2(5) . . ?
O7 C3 C1 117.0(5) . . ?
O4 C3 C1 116.7(5) . . ?
C10 C4 C8 121.0(6) . . ?
O5 C5 O1 122.3(5) . . ?
O5 C5 C8 125.0(5) . . ?
O1 C5 C8 112.7(5) . . ?
C8 C6 C11 118.6(6) . . ?
C11 C7 C10 120.9(6) . . ?
C6 C8 C4 119.4(5) . . ?
C6 C8 C5 123.3(5) . . ?
C4 C8 C5 117.4(5) . . ?
C16 C9 C20 122.5(6) . . ?
C16 C9 N1 120.3(6) . . ?
C20 C9 N1 117.2(6) . . ?
C7 C10 C4 118.7(6) . . ?
C7 C10 C15 121.6(6) . . ?
C4 C10 C15 119.7(6) . . ?
C7 C11 C6 121.4(6) . . ?
C18 C12 C26 119.8(9) . . ?
C18 C12 C14 122.7(6) . . ?
C26 C12 C14 117.5(9) . . ?
O3 C13 O6 126.8(5) . . ?
O3 C13 C2 118.5(5) . . ?
O6 C13 C2 114.6(5) . . ?
O8 C14 O2 123.0(6) . . ?
O8 C14 C12 126.2(6) . . ?
O2 C14 C12 110.8(6) . . ?
C9 C16 C22 118.3(7) . . ?
C24 C17 C22 119.1(7) . . ?
C24 C17 C25 120.5(7) . . ?
C22 C17 C25 120.4(7) . . ?
C12 C18 C19 120.2(8) . . ?
C23 C19 C18 120.3(12) . . ?
C23 C19 C27 119.2(10) . . ?
C18 C19 C27 120.5(10) . . ?
C9 C20 C24 116.9(7) . . ?
C23 C21 C26 120.6(9) . . ?
C17 C22 C16 120.9(8) . . ?
C19 C23 C21 121.2(10) . . ?
C17 C24 C20 122.3(8) . . ?
C17 C25 C17 112.4(8) . 2 ?
C12 C26 C21 117.7(12) . . ?
O9 C29 C29 150(8) . 2_556 ?
O9 C29 C28 131(4) . . ?
C29 C29 C28 79(5) 2_556 . ?

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.059

_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_C2
_database_code_depnum_ccdc_archive 'CCDC 1414400'
_audit_update_record             
;
2015-11-01 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C20 H16 O8 2-, C12 H14 N2 O 2+, 2(C4 H10 O), H2 O'
_chemical_formula_sum            'C40 H52 N2 O12'
_chemical_formula_weight         752.83

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

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

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

_cell_length_a                   7.7919(13)
_cell_length_b                   21.208(4)
_cell_length_c                   24.416(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4034.7(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             1608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9749
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18894
_diffrn_reflns_av_unetI/netI     0.1062
_diffrn_reflns_av_R_equivalents  0.1030
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.272
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             7072
_reflns_number_gt                4689
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.964

_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-2013 (Sheldrick, 2013)'
_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)+(0.1383P)²+2.1949P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1563 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   1.0(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         7072
_refine_ls_number_parameters     454
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0853
_refine_ls_wR_factor_ref         0.2477
_refine_ls_wR_factor_gt          0.2202
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.4225(6) 0.23834(19) 0.76057(19) 0.0264(11) Uani 1 1 d . . . . .
O2 O 0.3505(6) 0.36690(19) 0.7316(2) 0.0278(11) Uani 1 1 d . . . . .
O3 O 0.4280(7) 0.1402(2) 0.7265(2) 0.0361(13) Uani 1 1 d . . . . .
O4 O 0.7870(7) 0.3168(2) 0.7396(2) 0.0337(12) Uani 1 1 d . . . . .
O5 O 0.6111(7) 0.3526(2) 0.8043(2) 0.0361(13) Uani 1 1 d . . . . .
O6 O 0.2998(7) 0.3515(3) 0.8587(2) 0.0435(14) Uiso 1 1 d . . . . .
O7 O 0.5110(7) 0.4531(2) 0.7192(2) 0.0414(14) Uani 1 1 d . . . . .
O8 O -0.0799(8) 0.0632(2) 0.9272(2) 0.0437(14) Uani 1 1 d . . . . .
O9 O 0.3119(8) 0.2658(3) 0.6200(2) 0.0447(15) Uani 1 1 d . . . . .
O10 O 0.1477(7) 0.2458(2) 0.6925(2) 0.0378(13) Uani 1 1 d . . . . .
C1 C 0.3787(10) 0.4299(3) 0.7339(3) 0.0290(17) Uani 1 1 d . . . . .
N1 N 0.0612(10) 0.2767(3) 0.8004(3) 0.0339(15) Uani 1 1 d . . . . .
H1 H 0.150(11) 0.305(4) 0.822(3) 0.03(2) Uiso 1 1 d . . . . .
H2 H -0.012(12) 0.303(4) 0.785(3) 0.04(2) Uiso 1 1 d . . . . .
H3 H 0.113(11) 0.264(4) 0.772(4) 0.03(2) Uiso 1 1 d . . . . .
N2 N 0.0933(9) -0.1831(3) 0.8665(3) 0.0372(16) Uani 1 1 d . . . . .
H4 H 0.1793 -0.1968 0.8886 0.056 Uiso 1 1 calc R U . . .
H5 H 0.1290 -0.1840 0.8310 0.056 Uiso 1 1 calc R U . . .
H6 H 0.0002 -0.2086 0.8704 0.056 Uiso 1 1 calc R U . . .
C2 C 0.4343(10) 0.1741(3) 0.7660(3) 0.0287(16) Uani 1 1 d . . . . .
C3 C 0.1325(11) 0.5606(3) 0.8023(3) 0.0329(18) Uani 1 1 d . . . . .
C4 C 0.4455(9) 0.2631(3) 0.7065(3) 0.0251(15) Uani 1 1 d . . . . .
H7 H 0.5423 0.2399 0.6887 0.030 Uiso 1 1 calc R U . . .
C5 C 0.6453(10) 0.3350(3) 0.7573(3) 0.0295(17) Uani 1 1 d . . . . .
C6 C 0.4581(11) 0.0910(3) 0.8348(3) 0.0350(18) Uani 1 1 d . . . . .
H8 H 0.4350 0.0607 0.8072 0.042 Uiso 1 1 calc R U . . .
C7 C 0.2874(11) 0.2572(3) 0.6702(3) 0.0326(18) Uani 1 1 d . . . . .
C8 C 0.0467(10) -0.1181(3) 0.8815(3) 0.0341(18) Uani 1 1 d . . . . .
C9 C 0.4611(10) 0.1556(3) 0.8226(3) 0.0285(17) Uani 1 1 d . . . . .
C10 C 0.4998(9) 0.3318(3) 0.7146(3) 0.0261(16) Uani 1 1 d . . . . .
H9 H 0.5423 0.3491 0.6790 0.031 Uiso 1 1 calc R U . . .
C11 C 0.2319(9) 0.4659(3) 0.7566(3) 0.0275(16) Uani 1 1 d . . . . .
C12 C -0.0341(11) 0.0029(3) 0.9096(3) 0.0354(18) Uani 1 1 d . . . . .
C13 C 0.0257(10) 0.2203(3) 0.8329(3) 0.0316(17) Uani 1 1 d . . . . .
C14 C -0.0335(11) 0.5371(4) 0.7990(3) 0.0397(19) Uani 1 1 d . . . . .
H10 H -0.1257 0.5614 0.8133 0.048 Uiso 1 1 calc R U . . .
C15 C 0.2670(11) 0.5247(3) 0.7802(3) 0.0301(17) Uani 1 1 d . . . . .
H11 H 0.3813 0.5402 0.7811 0.036 Uiso 1 1 calc R U . . .
C16 C 0.5009(11) 0.1990(3) 0.8635(3) 0.0359(19) Uani 1 1 d . . . . .
H12 H 0.5063 0.2426 0.8547 0.043 Uiso 1 1 calc R U . . .
C17 C -0.0385(10) 0.1141(3) 0.8941(3) 0.0350(18) Uani 1 1 d . . . . .
C18 C 0.0648(10) 0.4428(3) 0.7556(3) 0.0332(17) Uani 1 1 d . . . . .
H13 H 0.0422 0.4021 0.7411 0.040 Uiso 1 1 calc R U . . .
O11 O 0.6405(11) 0.2725(4) 0.5729(3) 0.080(2) Uiso 1 1 d . . . . .
C19 C 0.0699(12) 0.2187(4) 0.8872(3) 0.044(2) Uani 1 1 d . . . . .
H14 H 0.1232 0.2543 0.9035 0.053 Uiso 1 1 calc R U . . .
C20 C 0.1052(10) -0.0086(4) 0.8779(3) 0.0384(19) Uani 1 1 d . . . . .
H15 H 0.1737 0.0255 0.8654 0.046 Uiso 1 1 calc R U . . .
C21 C -0.0678(11) 0.4791(4) 0.7756(4) 0.044(2) Uani 1 1 d . . . . .
H16 H -0.1826 0.4643 0.7732 0.052 Uiso 1 1 calc R U . . .
C22 C 0.0371(12) 0.1651(4) 0.9185(3) 0.044(2) Uani 1 1 d . . . . .
H17 H 0.0668 0.1640 0.9563 0.053 Uiso 1 1 calc R U . . .
C23 C -0.0492(11) 0.1688(4) 0.8087(3) 0.040(2) Uani 1 1 d . . . . .
H18 H -0.0791 0.1700 0.7710 0.048 Uiso 1 1 calc R U . . .
C24 C 0.5291(12) 0.1156(4) 0.9287(3) 0.049(2) Uani 1 1 d . . . . .
H19 H 0.5539 0.1016 0.9648 0.058 Uiso 1 1 calc R U . . .
C25 C 0.4898(12) 0.0725(4) 0.8886(4) 0.045(2) Uani 1 1 d . . . . .
H20 H 0.4842 0.0290 0.8978 0.054 Uiso 1 1 calc R U . . .
C26 C -0.0808(12) 0.1156(4) 0.8389(3) 0.042(2) Uani 1 1 d . . . . .
H21 H -0.1315 0.0798 0.8221 0.050 Uiso 1 1 calc R U . . .
C27 C 0.5326(12) 0.1801(4) 0.9165(3) 0.041(2) Uani 1 1 d . . . . .
C28 C -0.0957(12) -0.1069(4) 0.9140(4) 0.049(2) Uani 1 1 d . . . . .
H22 H -0.1640 -0.1411 0.9265 0.059 Uiso 1 1 calc R U . . .
C29 C 0.1479(11) -0.0695(4) 0.8637(3) 0.0391(19) Uani 1 1 d . . . . .
H23 H 0.2463 -0.0777 0.8419 0.047 Uiso 1 1 calc R U . . .
C30 C -0.1370(12) -0.0469(4) 0.9278(4) 0.049(2) Uani 1 1 d . . . . .
H24 H -0.2354 -0.0387 0.9496 0.059 Uiso 1 1 calc R U . . .
C31 C 0.1707(12) 0.6215(4) 0.8309(4) 0.043(2) Uani 1 1 d . . . . .
H25 H 0.0775 0.6515 0.8241 0.065 Uiso 1 1 calc R U . . .
H26 H 0.2788 0.6389 0.8170 0.065 Uiso 1 1 calc R U . . .
H27 H 0.1808 0.6140 0.8704 0.065 Uiso 1 1 calc R U . . .
O12 O 0.1644(14) 0.2001(5) 0.5360(4) 0.107(3) Uiso 1 1 d . . . . .
C32 C 0.5765(19) 0.2269(5) 0.9606(4) 0.076(4) Uani 1 1 d . . . . .
H28 H 0.6860 0.2152 0.9775 0.114 Uiso 1 1 calc R U . . .
H29 H 0.4860 0.2269 0.9884 0.114 Uiso 1 1 calc R U . . .
H30 H 0.5860 0.2691 0.9445 0.114 Uiso 1 1 calc R U . . .
C33 C 0.136(3) 0.1385(9) 0.5516(8) 0.131(6) Uiso 1 1 d . . . . .
H31 H 0.1119 0.1363 0.5918 0.157 Uiso 1 1 calc R U . . .
C34 C 0.430(3) 0.1131(9) 0.5719(8) 0.138(6) Uiso 1 1 d . . . . .
H32 H 0.4804 0.1529 0.5592 0.207 Uiso 1 1 calc R U . . .
H33 H 0.5129 0.0789 0.5663 0.207 Uiso 1 1 calc R U . . .
H34 H 0.4023 0.1164 0.6109 0.207 Uiso 1 1 calc R U . . .
C35 C 0.263(3) 0.0989(12) 0.5385(10) 0.179(9) Uiso 1 1 d . . . . .
H35 H 0.2874 0.1026 0.4988 0.215 Uiso 1 1 calc R U . . .
H36 H 0.2253 0.0551 0.5458 0.215 Uiso 1 1 calc R U . . .
C36 C -0.023(3) 0.1135(12) 0.5180(10) 0.180(9) Uiso 1 1 d . . . . .
H37 H -0.0595 0.0728 0.5329 0.269 Uiso 1 1 calc R U . . .
H38 H 0.0102 0.1082 0.4795 0.269 Uiso 1 1 calc R U . . .
H39 H -0.1169 0.1439 0.5206 0.269 Uiso 1 1 calc R U . . .
C37 C 0.517(3) 0.4200(8) 0.9226(8) 0.123(6) Uiso 1 1 d . . . . .
C38 C 0.367(3) 0.4088(11) 0.9397(10) 0.076(9) Uiso 0.53(3) 1 d . . P A 2
C39 C 0.148(5) 0.4194(14) 0.9141(13) 0.088(11) Uiso 0.47(3) 1 d . . P A 1
C40 C 0.034(3) 0.4028(8) 0.9094(7) 0.107(5) Uiso 1 1 d . . . . .
C41 C 0.279(2) 0.4042(8) 0.8926(7) 0.108(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.371(8) . ?
O1 C4 1.431(8) . ?
O2 C1 1.356(8) . ?
O2 C10 1.442(8) . ?
O3 C2 1.203(9) . ?
O4 C5 1.248(9) . ?
O5 C5 1.235(9) . ?
O6 C41 1.400(17) . ?
O7 C1 1.196(9) . ?
O8 C17 1.387(9) . ?
O8 C12 1.395(9) . ?
O9 C7 1.254(10) . ?
O10 C7 1.241(10) . ?
C1 C11 1.483(10) . ?
N1 C13 1.461(10) . ?
N2 C8 1.472(10) . ?
C2 C9 1.452(10) . ?
C3 C14 1.389(12) . ?
C3 C15 1.404(11) . ?
C3 C31 1.499(11) . ?
C4 C7 1.524(10) . ?
C4 C10 1.530(9) . ?
C5 C10 1.542(11) . ?
C6 C25 1.393(11) . ?
C6 C9 1.402(9) . ?
C8 C29 1.368(11) . ?
C8 C28 1.384(12) . ?
C9 C16 1.393(10) . ?
C11 C18 1.391(11) . ?
C11 C15 1.400(10) . ?
C12 C20 1.355(11) . ?
C12 C30 1.398(12) . ?
C13 C19 1.369(11) . ?
C13 C23 1.372(11) . ?
C14 C21 1.383(11) . ?
C16 C27 1.375(11) . ?
C17 C22 1.367(11) . ?
C17 C26 1.388(11) . ?
C18 C21 1.378(11) . ?
C19 C22 1.395(12) . ?
C20 C29 1.378(11) . ?
C23 C26 1.370(11) . ?
C24 C25 1.373(12) . ?
C24 C27 1.400(12) . ?
C27 C32 1.504(13) . ?
C28 C30 1.355(12) . ?
O12 C33 1.38(2) . ?
C33 C35 1.33(3) . ?
C33 C36 1.58(3) . ?
C34 C35 1.57(3) . ?
C37 C38 1.27(3) . ?
C37 C41 2.02(3) . ?
C38 C41 1.34(3) . ?
C39 C40 0.96(3) . ?
C39 C41 1.19(3) . ?
C40 C41 1.95(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C4 116.4(5) . . ?
C1 O2 C10 112.9(5) . . ?
C17 O8 C12 118.4(6) . . ?
O7 C1 O2 122.2(7) . . ?
O7 C1 C11 124.5(6) . . ?
O2 C1 C11 113.4(6) . . ?
O3 C2 O1 120.9(6) . . ?
O3 C2 C9 127.3(6) . . ?
O1 C2 C9 111.7(6) . . ?
C14 C3 C15 118.6(7) . . ?
C14 C3 C31 121.4(7) . . ?
C15 C3 C31 120.0(8) . . ?
O1 C4 C7 113.9(6) . . ?
O1 C4 C10 105.4(5) . . ?
C7 C4 C10 112.1(6) . . ?
O5 C5 O4 127.3(7) . . ?
O5 C5 C10 118.9(7) . . ?
O4 C5 C10 113.7(7) . . ?
C25 C6 C9 118.2(7) . . ?
O10 C7 O9 126.3(7) . . ?
O10 C7 C4 118.0(7) . . ?
O9 C7 C4 115.7(7) . . ?
C29 C8 C28 121.0(7) . . ?
C29 C8 N2 118.9(7) . . ?
C28 C8 N2 120.1(7) . . ?
C16 C9 C6 119.8(7) . . ?
C16 C9 C2 122.4(6) . . ?
C6 C9 C2 117.7(6) . . ?
O2 C10 C4 107.8(6) . . ?
O2 C10 C5 112.0(6) . . ?
C4 C10 C5 109.4(5) . . ?
C18 C11 C15 120.2(7) . . ?
C18 C11 C1 122.3(6) . . ?
C15 C11 C1 117.4(7) . . ?
C20 C12 O8 123.0(7) . . ?
C20 C12 C30 120.3(7) . . ?
O8 C12 C30 116.6(7) . . ?
C19 C13 C23 120.2(7) . . ?
C19 C13 N1 119.9(7) . . ?
C23 C13 N1 119.9(7) . . ?
C21 C14 C3 121.5(8) . . ?
C11 C15 C3 119.7(7) . . ?
C27 C16 C9 121.4(7) . . ?
C22 C17 O8 117.5(7) . . ?
C22 C17 C26 120.6(7) . . ?
O8 C17 C26 121.8(7) . . ?
C21 C18 C11 119.9(7) . . ?
C13 C19 C22 120.4(7) . . ?
C12 C20 C29 120.4(8) . . ?
C18 C21 C14 119.9(8) . . ?
C17 C22 C19 118.9(8) . . ?
C26 C23 C13 120.1(8) . . ?
C25 C24 C27 120.2(8) . . ?
C24 C25 C6 121.6(7) . . ?
C23 C26 C17 119.9(7) . . ?
C16 C27 C24 118.8(7) . . ?
C16 C27 C32 121.4(7) . . ?
C24 C27 C32 119.8(8) . . ?
C30 C28 C8 119.6(8) . . ?
C8 C29 C20 119.1(8) . . ?
C28 C30 C12 119.6(8) . . ?
C35 C33 O12 114(2) . . ?
C35 C33 C36 104.0(18) . . ?
O12 C33 C36 107.4(18) . . ?
C33 C35 C34 112(2) . . ?
C38 C37 C41 40.5(13) . . ?
C37 C38 C41 102(2) . . ?
C40 C39 C41 130(3) . . ?
C39 C40 C41 28(2) . . ?
C39 C41 O6 125(2) . . ?
C38 C41 O6 120.4(17) . . ?
C39 C41 C40 22.2(17) . . ?
C38 C41 C40 108.5(16) . . ?
O6 C41 C40 103.0(11) . . ?
C39 C41 C37 126(2) . . ?
C38 C41 C37 37.8(12) . . ?
O6 C41 C37 103.9(12) . . ?
C40 C41 C37 145.3(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 O2 C1 O7 5.0(10) . . . . ?
C10 O2 C1 C11 -174.2(6) . . . . ?
C4 O1 C2 O3 -15.0(10) . . . . ?
C4 O1 C2 C9 162.6(6) . . . . ?
C2 O1 C4 C7 79.3(8) . . . . ?
C2 O1 C4 C10 -157.3(6) . . . . ?
O1 C4 C7 O10 15.9(9) . . . . ?
C10 C4 C7 O10 -103.7(7) . . . . ?
O1 C4 C7 O9 -165.6(5) . . . . ?
C10 C4 C7 O9 74.7(8) . . . . ?
C25 C6 C9 C16 2.1(12) . . . . ?
C25 C6 C9 C2 177.7(7) . . . . ?
O3 C2 C9 C16 166.6(8) . . . . ?
O1 C2 C9 C16 -10.9(10) . . . . ?
O3 C2 C9 C6 -8.9(12) . . . . ?
O1 C2 C9 C6 173.7(7) . . . . ?
C1 O2 C10 C4 -172.8(6) . . . . ?
C1 O2 C10 C5 66.8(7) . . . . ?
O1 C4 C10 O2 -73.6(6) . . . . ?
C7 C4 C10 O2 50.8(8) . . . . ?
O1 C4 C10 C5 48.4(7) . . . . ?
C7 C4 C10 C5 172.9(6) . . . . ?
O5 C5 C10 O2 16.5(8) . . . . ?
O4 C5 C10 O2 -165.9(5) . . . . ?
O5 C5 C10 C4 -103.0(7) . . . . ?
O4 C5 C10 C4 74.7(8) . . . . ?
O7 C1 C11 C18 157.3(8) . . . . ?
O2 C1 C11 C18 -23.5(10) . . . . ?
O7 C1 C11 C15 -23.3(11) . . . . ?
O2 C1 C11 C15 155.9(6) . . . . ?
C17 O8 C12 C20 30.1(11) . . . . ?
C17 O8 C12 C30 -151.8(8) . . . . ?
C15 C3 C14 C21 1.2(12) . . . . ?
C31 C3 C14 C21 -176.1(7) . . . . ?
C18 C11 C15 C3 -0.6(10) . . . . ?
C1 C11 C15 C3 -179.9(6) . . . . ?
C14 C3 C15 C11 -1.5(10) . . . . ?
C31 C3 C15 C11 175.9(7) . . . . ?
C6 C9 C16 C27 -2.0(12) . . . . ?
C2 C9 C16 C27 -177.3(8) . . . . ?
C12 O8 C17 C22 -132.6(8) . . . . ?
C12 O8 C17 C26 51.2(11) . . . . ?
C15 C11 C18 C21 2.9(11) . . . . ?
C1 C11 C18 C21 -177.8(7) . . . . ?
C23 C13 C19 C22 -0.9(13) . . . . ?
N1 C13 C19 C22 -179.8(8) . . . . ?
O8 C12 C20 C29 177.3(8) . . . . ?
C30 C12 C20 C29 -0.7(13) . . . . ?
C11 C18 C21 C14 -3.1(12) . . . . ?
C3 C14 C21 C18 1.1(13) . . . . ?
O8 C17 C22 C19 -175.8(8) . . . . ?
C26 C17 C22 C19 0.5(13) . . . . ?
C13 C19 C22 C17 0.5(14) . . . . ?
C19 C13 C23 C26 0.3(13) . . . . ?
N1 C13 C23 C26 179.2(8) . . . . ?
C27 C24 C25 C6 2.1(14) . . . . ?
C9 C6 C25 C24 -2.2(13) . . . . ?
C13 C23 C26 C17 0.7(13) . . . . ?
C22 C17 C26 C23 -1.1(13) . . . . ?
O8 C17 C26 C23 175.0(8) . . . . ?
C9 C16 C27 C24 1.8(13) . . . . ?
C9 C16 C27 C32 179.7(9) . . . . ?
C25 C24 C27 C16 -1.8(13) . . . . ?
C25 C24 C27 C32 -179.8(10) . . . . ?
C29 C8 C28 C30 0.9(13) . . . . ?
N2 C8 C28 C30 179.8(8) . . . . ?
C28 C8 C29 C20 -0.9(12) . . . . ?
N2 C8 C29 C20 -179.8(7) . . . . ?
C12 C20 C29 C8 0.8(12) . . . . ?
C8 C28 C30 C12 -0.8(14) . . . . ?
C20 C12 C30 C28 0.8(14) . . . . ?
O8 C12 C30 C28 -177.4(8) . . . . ?
O12 C33 C35 C34 68(3) . . . . ?
C36 C33 C35 C34 -175.5(19) . . . . ?
C40 C39 C41 C38 -138(4) . . . . ?
C40 C39 C41 O6 -8(6) . . . . ?
C40 C39 C41 C37 -158(3) . . . . ?
C37 C38 C41 C39 -154(2) . . . . ?
C37 C38 C41 O6 72(2) . . . . ?
C37 C38 C41 C40 -169.3(15) . . . . ?

_refine_diff_density_max         0.648
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.077

_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_D1
_database_code_depnum_ccdc_archive 'CCDC 1414401'
_audit_update_record             
;
2015-11-01 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H17 O8, C13 H15 N2'
_chemical_formula_sum            'C33 H32 N2 O8'
_chemical_formula_weight         584.60

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      tetragonal
_space_group_IT_number           80
_space_group_name_H-M_alt        'I 41'
_space_group_name_Hall           'I 4bw'

_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'
'-y, x+1/2, z+1/4'
'y, -x+1/2, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1, z+3/4'
'y+1/2, -x+1, z+3/4'

_cell_length_a                   28.639(5)
_cell_length_b                   28.639(5)
_cell_length_c                   7.8757(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6460(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_F_000             2464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15524
_diffrn_reflns_av_unetI/netI     0.1174
_diffrn_reflns_av_R_equivalents  0.1030
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.005
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             5607
_reflns_number_gt                3031
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_max     0.962
_reflns_Friedel_fraction_full    0.938

_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-2013 (Sheldrick, 2013)'
_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)+(0.0657P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1021 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -2.6(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         5607
_refine_ls_number_parameters     396
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1503
_refine_ls_wR_factor_gt          0.1313
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_restrained_S_all      0.910
_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 0.39094(12) 0.45360(12) 0.3691(5) 0.0357(9) Uani 1 1 d . . . . .
O2 O 0.45362(12) 0.39102(12) 0.2685(5) 0.0361(9) Uani 1 1 d . . . . .
O3 O 0.45090(14) 0.42491(13) -0.0422(5) 0.0442(10) Uani 1 1 d . . . . .
H1 H 0.4407 0.4364 -0.1332 0.066 Uiso 0.46(13) 1 calc R U P . .
O4 O 0.42505(13) 0.45071(14) 0.6792(5) 0.0446(10) Uani 1 1 d . . . . .
H2 H 0.4374 0.4443 0.7730 0.067 Uiso 0.54(13) 1 calc R U P . .
O5 O 0.52391(14) 0.36912(14) 0.1666(6) 0.0525(11) Uani 1 1 d . . . . .
O6 O 0.49808(14) 0.44199(14) 0.5830(5) 0.0488(11) Uani 1 1 d . . . . .
O7 O 0.36894(14) 0.52386(14) 0.4719(6) 0.0515(11) Uani 1 1 d . . . . .
O8 O 0.44188(14) 0.49806(14) 0.0549(5) 0.0479(11) Uani 1 1 d . . . . .
C1 C 0.46525(18) 0.43955(18) 0.2491(6) 0.0297(12) Uani 1 1 d . . . . .
H3 H 0.4997 0.4438 0.2642 0.036 Uiso 1 1 calc R U . . .
C2 C 0.43974(18) 0.46519(18) 0.3882(7) 0.0311(13) Uani 1 1 d . . . . .
H4 H 0.4441 0.4996 0.3731 0.037 Uiso 1 1 calc R U . . .
C3 C 0.4847(2) 0.35914(19) 0.2098(7) 0.0383(14) Uani 1 1 d . . . . .
C4 C 0.4562(2) 0.45105(19) 0.5639(7) 0.0360(14) Uani 1 1 d . . . . .
C5 C 0.45111(18) 0.4565(2) 0.0739(7) 0.0350(14) Uani 1 1 d . . . . .
C6 C 0.4640(2) 0.31239(19) 0.2077(8) 0.0464(15) Uani 1 1 d . . . . .
C7 C 0.3122(2) 0.4639(2) 0.4287(8) 0.0473(16) Uani 1 1 d . . . . .
C8 C 0.35909(19) 0.4847(2) 0.4284(8) 0.0423(15) Uani 1 1 d . . . . .
C9 C 0.2741(2) 0.4930(3) 0.4406(11) 0.077(2) Uani 1 1 d . . . . .
H5 H 0.2782 0.5258 0.4456 0.092 Uiso 1 1 calc R U . . .
C10 C 0.4931(3) 0.2738(2) 0.1951(11) 0.077(2) Uani 1 1 d . . . . .
H6 H 0.5260 0.2779 0.1891 0.092 Uiso 1 1 calc R U . . .
C11 C 0.5772(3) 0.3533(3) 0.5451(10) 0.072(2) Uani 1 1 d . . . . .
H7 H 0.5623 0.3780 0.4855 0.086 Uiso 1 1 calc R U . . .
C12 C 0.5772(3) 0.1470(3) 0.3423(10) 0.070(2) Uani 1 1 d . . . . .
H8 H 0.5620 0.1224 0.4014 0.084 Uiso 1 1 calc R U . . .
C13 C 0.5726(2) 0.1503(3) 0.1705(10) 0.081(3) Uani 1 1 d . . . . .
C14 C 0.3051(3) 0.4168(3) 0.4247(12) 0.086(3) Uani 1 1 d . . . . .
H9 H 0.3311 0.3963 0.4180 0.104 Uiso 1 1 calc R U . . .
N1 N 0.5476(2) 0.1149(4) 0.0782(9) 0.124(3) Uani 1 1 d . . . . .
H10 H 0.5676 0.0916 0.0489 0.186 Uiso 0.83(18) 1 calc R U P . .
H11 H 0.5350 0.1276 -0.0173 0.186 Uiso 1 1 calc R U . . .
H12 H 0.5244 0.1032 0.1446 0.186 Uiso 1 1 calc R U . . .
C15 C 0.6036(2) 0.3210(2) 0.4576(10) 0.067(2) Uani 1 1 d . . . . .
H13 H 0.6062 0.3234 0.3377 0.081 Uiso 1 1 calc R U . . .
C16 C 0.4166(3) 0.3052(3) 0.2111(13) 0.088(3) Uani 1 1 d . . . . .
H14 H 0.3960 0.3312 0.2172 0.106 Uiso 1 1 calc R U . . .
C17 C 0.2212(3) 0.4277(4) 0.4391(12) 0.087(3) Uani 1 1 d . . . . .
C18 C 0.4276(4) 0.2214(3) 0.2000(13) 0.092(3) Uani 1 1 d . . . . .
C19 C 0.5725(2) 0.3499(3) 0.7176(10) 0.082(3) Uani 1 1 d . . . . .
C20 C 0.6034(2) 0.1789(3) 0.4306(10) 0.070(2) Uani 1 1 d . . . . .
H15 H 0.6061 0.1764 0.5505 0.084 Uiso 1 1 calc R U . . .
C21 C 0.6550(2) 0.2497(3) 0.4434(16) 0.102(3) Uani 1 1 d . . . . .
H16 H 0.6757 0.2665 0.3634 0.122 Uiso 1 1 calc R U . . .
H17 H 0.6751 0.2325 0.5243 0.122 Uiso 1 1 calc R U . . .
C22 C 0.6264(2) 0.2852(3) 0.5411(14) 0.079(3) Uani 1 1 d . . . . .
C23 C 0.6262(2) 0.2149(3) 0.3448(13) 0.077(3) Uani 1 1 d . . . . .
N2 N 0.5478(2) 0.3863(4) 0.8086(9) 0.128(4) Uani 1 1 d . . . . .
H18 H 0.5385 0.3752 0.9115 0.193 Uiso 1 1 calc R U . . .
H19 H 0.5223 0.3952 0.7477 0.193 Uiso 1 1 calc R U . . .
H20 H 0.5670 0.4112 0.8238 0.193 Uiso 0.17(18) 1 calc R U P . .
C24 C 0.6212(3) 0.2825(3) 0.7137(15) 0.100(3) Uani 1 1 d . . . . .
H21 H 0.6364 0.2580 0.7734 0.120 Uiso 1 1 calc R U . . .
C25 C 0.4740(4) 0.2290(3) 0.1913(13) 0.094(3) Uani 1 1 d . . . . .
H22 H 0.4943 0.2030 0.1823 0.113 Uiso 1 1 calc R U . . .
C26 C 0.5947(3) 0.1865(4) 0.0838(13) 0.110(4) Uani 1 1 d . . . . .
H23 H 0.5913 0.1896 -0.0356 0.132 Uiso 1 1 calc R U . . .
C27 C 0.6211(3) 0.2171(4) 0.1729(15) 0.103(4) Uani 1 1 d . . . . .
H24 H 0.6367 0.2413 0.1129 0.124 Uiso 1 1 calc R U . . .
C28 C 0.2293(3) 0.4738(4) 0.4453(13) 0.092(3) Uani 1 1 d . . . . .
H25 H 0.2034 0.4944 0.4534 0.111 Uiso 1 1 calc R U . . .
C29 C 0.5949(3) 0.3135(4) 0.8026(12) 0.105(4) Uani 1 1 d . . . . .
H26 H 0.5919 0.3105 0.9221 0.126 Uiso 1 1 calc R U . . .
C30 C 0.4075(4) 0.1712(3) 0.1945(15) 0.137(4) Uani 1 1 d . . . . .
H27 H 0.3798 0.1706 0.1211 0.205 Uiso 1 1 calc R U . . .
H28 H 0.3987 0.1614 0.3094 0.205 Uiso 1 1 calc R U . . .
H29 H 0.4311 0.1498 0.1494 0.205 Uiso 1 1 calc R U . . .
C31 C 0.2600(3) 0.3985(3) 0.4304(16) 0.116(4) Uani 1 1 d . . . . .
H30 H 0.2557 0.3656 0.4283 0.139 Uiso 1 1 calc R U . . .
C32 C 0.3984(3) 0.2602(3) 0.2057(16) 0.118(4) Uani 1 1 d . . . . .
H31 H 0.3655 0.2559 0.2060 0.142 Uiso 1 1 calc R U . . .
C33 C 0.1714(3) 0.4075(4) 0.4436(15) 0.136(4) Uani 1 1 d . . . . .
H32 H 0.1635 0.3989 0.5605 0.204 Uiso 1 1 calc R U . . .
H33 H 0.1699 0.3798 0.3709 0.204 Uiso 1 1 calc R U . . .
H34 H 0.1493 0.4310 0.4025 0.204 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 C8 1.359(6) . ?
O1 C2 1.444(6) . ?
O2 C3 1.357(6) . ?
O2 C1 1.438(6) . ?
O3 C5 1.285(6) . ?
O3 H1 0.8400 . ?
O4 C4 1.273(6) . ?
O4 H2 0.8400 . ?
O5 C3 1.207(7) . ?
O6 C4 1.237(6) . ?
O7 C8 1.205(7) . ?
O8 C5 1.229(6) . ?
C1 C2 1.508(6) . ?
C1 C5 1.518(7) . ?
C1 H3 1.0000 . ?
C2 C4 1.517(7) . ?
C2 H4 1.0000 . ?
C3 C6 1.464(8) . ?
C6 C16 1.375(9) . ?
C6 C10 1.387(8) . ?
C7 C14 1.365(9) . ?
C7 C9 1.376(8) . ?
C7 C8 1.470(8) . ?
C9 C28 1.395(11) . ?
C9 H5 0.9500 . ?
C10 C25 1.397(11) . ?
C10 H6 0.9500 . ?
C11 C19 1.368(11) . ?
C11 C15 1.380(10) . ?
C11 H7 0.9500 . ?
C12 C13 1.363(11) . ?
C12 C20 1.372(10) . ?
C12 H8 0.9500 . ?
C13 C26 1.391(11) . ?
C13 N1 1.438(11) . ?
C14 C31 1.394(11) . ?
C14 H9 0.9500 . ?
N1 H10 0.9100 . ?
N1 H11 0.9100 . ?
N1 H12 0.9100 . ?
C15 C22 1.381(10) . ?
C15 H13 0.9500 . ?
C16 C32 1.391(11) . ?
C16 H14 0.9500 . ?
C17 C28 1.342(12) . ?
C17 C31 1.392(11) . ?
C17 C33 1.539(10) . ?
C18 C25 1.346(12) . ?
C18 C32 1.393(12) . ?
C18 C30 1.550(10) . ?
C19 C29 1.394(11) . ?
C19 N2 1.449(11) . ?
C20 C23 1.395(10) . ?
C20 H15 0.9500 . ?
C21 C23 1.509(12) . ?
C21 C22 1.516(12) . ?
C21 H16 0.9900 . ?
C21 H17 0.9900 . ?
C22 C24 1.370(13) . ?
C23 C27 1.363(13) . ?
N2 H18 0.9100 . ?
N2 H19 0.9100 . ?
N2 H20 0.9100 . ?
C24 C29 1.358(13) . ?
C24 H21 0.9500 . ?
C25 H22 0.9500 . ?
C26 C27 1.355(14) . ?
C26 H23 0.9500 . ?
C27 H24 0.9500 . ?
C28 H25 0.9500 . ?
C29 H26 0.9500 . ?
C30 H27 0.9800 . ?
C30 H28 0.9800 . ?
C30 H29 0.9800 . ?
C31 H30 0.9500 . ?
C32 H31 0.9500 . ?
C33 H32 0.9800 . ?
C33 H33 0.9800 . ?
C33 H34 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C2 117.6(4) . . ?
C3 O2 C1 117.5(4) . . ?
C5 O3 H1 109.5 . . ?
C4 O4 H2 109.5 . . ?
O2 C1 C2 106.3(4) . . ?
O2 C1 C5 110.1(4) . . ?
C2 C1 C5 112.1(4) . . ?
O2 C1 H3 109.4 . . ?
C2 C1 H3 109.4 . . ?
C5 C1 H3 109.4 . . ?
O1 C2 C1 106.3(4) . . ?
O1 C2 C4 109.5(4) . . ?
C1 C2 C4 112.5(4) . . ?
O1 C2 H4 109.5 . . ?
C1 C2 H4 109.5 . . ?
C4 C2 H4 109.5 . . ?
O5 C3 O2 123.2(5) . . ?
O5 C3 C6 126.2(5) . . ?
O2 C3 C6 110.7(5) . . ?
O6 C4 O4 126.3(5) . . ?
O6 C4 C2 117.9(5) . . ?
O4 C4 C2 115.8(5) . . ?
O8 C5 O3 126.4(5) . . ?
O8 C5 C1 118.5(5) . . ?
O3 C5 C1 115.1(5) . . ?
C16 C6 C10 118.5(6) . . ?
C16 C6 C3 122.5(6) . . ?
C10 C6 C3 119.0(6) . . ?
C14 C7 C9 118.8(6) . . ?
C14 C7 C8 122.5(6) . . ?
C9 C7 C8 118.6(6) . . ?
O7 C8 O1 123.4(5) . . ?
O7 C8 C7 126.2(5) . . ?
O1 C8 C7 110.3(5) . . ?
C7 C9 C28 119.5(7) . . ?
C7 C9 H5 120.2 . . ?
C28 C9 H5 120.2 . . ?
C6 C10 C25 119.8(7) . . ?
C6 C10 H6 120.1 . . ?
C25 C10 H6 120.1 . . ?
C19 C11 C15 120.1(8) . . ?
C19 C11 H7 120.0 . . ?
C15 C11 H7 120.0 . . ?
C13 C12 C20 120.7(8) . . ?
C13 C12 H8 119.7 . . ?
C20 C12 H8 119.7 . . ?
C12 C13 C26 119.7(9) . . ?
C12 C13 N1 120.0(8) . . ?
C26 C13 N1 120.2(8) . . ?
C7 C14 C31 120.5(7) . . ?
C7 C14 H9 119.7 . . ?
C31 C14 H9 119.7 . . ?
C13 N1 H10 109.5 . . ?
C13 N1 H11 109.5 . . ?
H10 N1 H11 109.5 . . ?
C13 N1 H12 109.5 . . ?
H10 N1 H12 109.5 . . ?
H11 N1 H12 109.5 . . ?
C11 C15 C22 121.3(8) . . ?
C11 C15 H13 119.4 . . ?
C22 C15 H13 119.4 . . ?
C6 C16 C32 120.5(7) . . ?
C6 C16 H14 119.7 . . ?
C32 C16 H14 119.7 . . ?
C28 C17 C31 117.1(8) . . ?
C28 C17 C33 121.9(9) . . ?
C31 C17 C33 121.0(9) . . ?
C25 C18 C32 117.7(7) . . ?
C25 C18 C30 121.1(9) . . ?
C32 C18 C30 121.1(10) . . ?
C11 C19 C29 119.0(9) . . ?
C11 C19 N2 119.2(7) . . ?
C29 C19 N2 121.6(8) . . ?
C12 C20 C23 120.1(8) . . ?
C12 C20 H15 119.9 . . ?
C23 C20 H15 119.9 . . ?
C23 C21 C22 114.3(6) . . ?
C23 C21 H16 108.7 . . ?
C22 C21 H16 108.7 . . ?
C23 C21 H17 108.7 . . ?
C22 C21 H17 108.7 . . ?
H16 C21 H17 107.6 . . ?
C24 C22 C15 117.6(9) . . ?
C24 C22 C21 121.7(8) . . ?
C15 C22 C21 120.7(10) . . ?
C27 C23 C20 117.8(9) . . ?
C27 C23 C21 122.6(8) . . ?
C20 C23 C21 119.6(9) . . ?
C19 N2 H18 109.5 . . ?
C19 N2 H19 109.5 . . ?
H18 N2 H19 109.5 . . ?
C19 N2 H20 109.5 . . ?
H18 N2 H20 109.5 . . ?
H19 N2 H20 109.5 . . ?
C29 C24 C22 122.3(8) . . ?
C29 C24 H21 118.9 . . ?
C22 C24 H21 118.9 . . ?
C18 C25 C10 122.4(7) . . ?
C18 C25 H22 118.8 . . ?
C10 C25 H22 118.8 . . ?
C27 C26 C13 118.8(9) . . ?
C27 C26 H23 120.6 . . ?
C13 C26 H23 120.6 . . ?
C26 C27 C23 122.9(8) . . ?
C26 C27 H24 118.6 . . ?
C23 C27 H24 118.6 . . ?
C17 C28 C9 123.0(7) . . ?
C17 C28 H25 118.5 . . ?
C9 C28 H25 118.5 . . ?
C24 C29 C19 119.8(9) . . ?
C24 C29 H26 120.1 . . ?
C19 C29 H26 120.1 . . ?
C18 C30 H27 109.5 . . ?
C18 C30 H28 109.5 . . ?
H27 C30 H28 109.5 . . ?
C18 C30 H29 109.5 . . ?
H27 C30 H29 109.5 . . ?
H28 C30 H29 109.5 . . ?
C17 C31 C14 121.1(8) . . ?
C17 C31 H30 119.5 . . ?
C14 C31 H30 119.5 . . ?
C16 C32 C18 121.0(9) . . ?
C16 C32 H31 119.5 . . ?
C18 C32 H31 119.5 . . ?
C17 C33 H32 109.5 . . ?
C17 C33 H33 109.5 . . ?
H32 C33 H33 109.5 . . ?
C17 C33 H34 109.5 . . ?
H32 C33 H34 109.5 . . ?
H33 C33 H34 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 O2 C1 C2 -153.8(4) . . . . ?
C3 O2 C1 C5 84.6(5) . . . . ?
C8 O1 C2 C1 -154.1(4) . . . . ?
C8 O1 C2 C4 84.2(5) . . . . ?
O2 C1 C2 O1 -56.0(4) . . . . ?
C5 C1 C2 O1 64.3(5) . . . . ?
O2 C1 C2 C4 63.8(5) . . . . ?
C5 C1 C2 C4 -175.8(4) . . . . ?
C1 O2 C3 O5 11.5(8) . . . . ?
C1 O2 C3 C6 -168.7(4) . . . . ?
O1 C2 C4 O6 153.7(5) . . . . ?
C1 C2 C4 O6 35.7(7) . . . . ?
O1 C2 C4 O4 -27.8(6) . . . . ?
C1 C2 C4 O4 -145.8(5) . . . . ?
O2 C1 C5 O8 153.1(5) . . . . ?
C2 C1 C5 O8 35.0(7) . . . . ?
O2 C1 C5 O3 -28.1(6) . . . . ?
C2 C1 C5 O3 -146.2(5) . . . . ?
O5 C3 C6 C16 -160.8(7) . . . . ?
O2 C3 C6 C16 19.4(9) . . . . ?
O5 C3 C6 C10 16.6(10) . . . . ?
O2 C3 C6 C10 -163.2(6) . . . . ?
C2 O1 C8 O7 11.5(8) . . . . ?
C2 O1 C8 C7 -169.2(4) . . . . ?
C14 C7 C8 O7 -160.9(7) . . . . ?
C9 C7 C8 O7 16.3(10) . . . . ?
C14 C7 C8 O1 19.9(9) . . . . ?
C9 C7 C8 O1 -162.9(6) . . . . ?
C14 C7 C9 C28 -1.1(12) . . . . ?
C8 C7 C9 C28 -178.4(7) . . . . ?
C16 C6 C10 C25 -1.9(12) . . . . ?
C3 C6 C10 C25 -179.4(7) . . . . ?
C20 C12 C13 C26 -0.1(13) . . . . ?
C20 C12 C13 N1 175.8(7) . . . . ?
C9 C7 C14 C31 0.8(13) . . . . ?
C8 C7 C14 C31 178.0(9) . . . . ?
C19 C11 C15 C22 -1.1(12) . . . . ?
C10 C6 C16 C32 1.4(13) . . . . ?
C3 C6 C16 C32 178.8(9) . . . . ?
C15 C11 C19 C29 0.2(13) . . . . ?
C15 C11 C19 N2 175.1(7) . . . . ?
C13 C12 C20 C23 -0.7(12) . . . . ?
C11 C15 C22 C24 1.1(11) . . . . ?
C11 C15 C22 C21 179.4(7) . . . . ?
C23 C21 C22 C24 104.7(11) . . . . ?
C23 C21 C22 C15 -73.5(10) . . . . ?
C12 C20 C23 C27 0.5(11) . . . . ?
C12 C20 C23 C21 180.0(7) . . . . ?
C22 C21 C23 C27 104.6(11) . . . . ?
C22 C21 C23 C20 -74.9(10) . . . . ?
C15 C22 C24 C29 -0.4(14) . . . . ?
C21 C22 C24 C29 -178.7(8) . . . . ?
C32 C18 C25 C10 2.7(15) . . . . ?
C30 C18 C25 C10 179.6(9) . . . . ?
C6 C10 C25 C18 -0.2(14) . . . . ?
C12 C13 C26 C27 1.2(14) . . . . ?
N1 C13 C26 C27 -174.7(9) . . . . ?
C13 C26 C27 C23 -1.5(16) . . . . ?
C20 C23 C27 C26 0.7(14) . . . . ?
C21 C23 C27 C26 -178.8(8) . . . . ?
C31 C17 C28 C9 1.1(15) . . . . ?
C33 C17 C28 C9 -179.7(9) . . . . ?
C7 C9 C28 C17 0.1(14) . . . . ?
C22 C24 C29 C19 -0.4(15) . . . . ?
C11 C19 C29 C24 0.5(14) . . . . ?
N2 C19 C29 C24 -174.2(9) . . . . ?
C28 C17 C31 C14 -1.4(16) . . . . ?
C33 C17 C31 C14 179.4(10) . . . . ?
C7 C14 C31 C17 0.5(17) . . . . ?
C6 C16 C32 C18 1.2(17) . . . . ?
C25 C18 C32 C16 -3.2(17) . . . . ?
C30 C18 C32 C16 179.9(10) . . . . ?

_refine_diff_density_max         0.325
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-4


#==============================================================================
# start Validation Reply Form
_vrf_PLAT601_D1                  
;
PROBLEM:  Structure Contains Solvent Accessible VOIDS of .        258 Ang3  
RESPONSE: This is due to the diffused distribution of electron density derived from solvent.
;
# 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_D2
_database_code_depnum_ccdc_archive 'CCDC 1414403'
_audit_update_record             
;
2015-11-01 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 O8 2-, C12 H14 N2 O 2+, 2(C5 H12 O)'
_chemical_formula_sum            'C42 H54 N2 O11'
_chemical_formula_weight         762.87

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

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

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

_cell_length_a                   7.7836(8)
_cell_length_b                   22.234(2)
_cell_length_c                   24.890(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4307.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20564
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_av_R_equivalents  0.1016
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.228
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             7561
_reflns_number_gt                5498
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.964

_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-2013 (Sheldrick, 2013)'
_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)+(0.1325P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1975 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.8(7)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         7561
_refine_ls_number_parameters     523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.2087
_refine_ls_wR_factor_gt          0.1966
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 -0.3281(5) 0.74607(15) 0.26064(15) 0.0390(9) Uani 1 1 d . . . . .
O2 O 0.0359(5) 0.82600(13) 0.27627(14) 0.0356(8) Uani 1 1 d . . . . .
O3 O -0.0037(5) 0.91642(15) 0.23817(16) 0.0484(10) Uani 1 1 d . . . . .
O4 O 0.1097(4) 0.70011(15) 0.25017(14) 0.0353(8) Uani 1 1 d . . . . .
O5 O -0.0498(5) 0.61735(16) 0.23634(17) 0.0474(10) Uani 1 1 d . . . . .
O6 O -0.1448(5) 0.71612(17) 0.32409(15) 0.0427(10) Uani 1 1 d . . . . .
O7 O 0.6137(6) 1.01046(17) 0.41181(16) 0.0494(11) Uani 1 1 d . . . . .
O8 O 0.1726(6) 0.73043(17) 0.37474(16) 0.0462(10) Uani 1 1 d . . . . .
H1 H 0.059(8) 0.718(3) 0.355(2) 0.046(16) Uiso 1 1 d . . . . .
O9 O 0.1399(7) 0.79078(19) 0.13959(19) 0.0645(13) Uani 1 1 d . . . . .
N1 N 0.4044(7) 0.7973(2) 0.3126(2) 0.0411(11) Uani 1 1 d . . . . .
H2 H 0.505(9) 0.771(3) 0.305(2) 0.052(17) Uiso 1 1 d . . . . .
H3 H 0.331(9) 0.769(3) 0.328(3) 0.060(19) Uiso 1 1 d . . . . .
H4 H 0.323(9) 0.803(3) 0.283(3) 0.060(19) Uiso 1 1 d . . . . .
O10 O 0.3073(6) 0.81693(19) 0.20845(19) 0.0577(12) Uani 1 1 d . . . . .
C1 C 0.0842(7) 0.6396(2) 0.2508(2) 0.0353(12) Uani 1 1 d . . . . .
C2 C -0.0422(7) 0.7333(2) 0.2344(2) 0.0348(12) Uani 1 1 d . . . . .
H5 H -0.0884 0.7159 0.2003 0.042 Uiso 1 1 calc R U . . .
C3 C 0.0161(7) 0.8868(2) 0.2777(2) 0.0353(12) Uani 1 1 d . . . . .
C4 C 0.2095(7) 0.5448(2) 0.2834(2) 0.0366(12) Uani 1 1 d . . . . .
H6 H 0.0993 0.5268 0.2801 0.044 Uiso 1 1 calc R U . . .
C5 C 0.4582(7) 0.8537(2) 0.3380(2) 0.0386(13) Uani 1 1 d . . . . .
N2 N 0.4474(7) 1.24235(19) 0.3417(2) 0.0471(13) Uani 1 1 d . . . . .
H7 H 0.3990 1.2414 0.3031 0.059(18) Uiso 1 1 calc R . . . .
H8 H 0.5552 1.2694 0.3428 0.10(3) Uiso 1 1 calc R . . . .
H9 H 0.3554 1.2593 0.3675 0.059(19) Uiso 1 1 calc R . . . .
C6 C 0.1675(8) 0.8037(2) 0.1882(3) 0.0453(15) Uani 1 1 d . . . . .
C7 C 0.2330(7) 0.6055(2) 0.2706(2) 0.0329(12) Uani 1 1 d . . . . .
C8 C 0.4942(8) 1.1807(2) 0.3585(2) 0.0416(13) Uani 1 1 d . . . . .
C9 C 0.0095(7) 0.7989(2) 0.2245(2) 0.0344(12) Uani 1 1 d . . . . .
H10 H -0.0884 0.8199 0.2065 0.041 Uiso 1 1 calc R U . . .
C10 C 0.5713(7) 1.0664(2) 0.3910(2) 0.0400(13) Uani 1 1 d . . . . .
C11 C -0.1819(7) 0.7303(2) 0.2778(2) 0.0350(12) Uani 1 1 d . . . . .
C12 C 0.3485(8) 0.5111(2) 0.3012(2) 0.0435(14) Uani 1 1 d . . . . .
H11 H 0.3310 0.4702 0.3108 0.052 Uiso 1 1 calc R U . . .
C13 C 0.0422(8) 0.9709(2) 0.3428(3) 0.0476(15) Uani 1 1 d . . . . .
H12 H 0.0643 0.9973 0.3136 0.057 Uiso 1 1 calc R U . . .
C14 C 0.5580(7) 0.9590(2) 0.3851(2) 0.0425(14) Uani 1 1 d . . . . .
C15 C 0.0156(7) 0.9095(2) 0.3336(2) 0.0390(13) Uani 1 1 d . . . . .
C16 C 0.5358(8) 0.8972(2) 0.3076(2) 0.0429(13) Uani 1 1 d . . . . .
H13 H 0.5537 0.8910 0.2703 0.051 Uiso 1 1 calc R U . . .
C17 C 0.5329(8) 0.5958(2) 0.2933(3) 0.0499(15) Uani 1 1 d . . . . .
H14 H 0.6433 0.6136 0.2968 0.060 Uiso 1 1 calc R U . . .
C18 C -0.0175(8) 0.8719(2) 0.3768(2) 0.0476(15) Uani 1 1 d . . . . .
H15 H -0.0337 0.8301 0.3710 0.057 Uiso 1 1 calc R U . . .
C19 C 0.3856(8) 1.1346(3) 0.3449(2) 0.0478(15) Uani 1 1 d . . . . .
H16 H 0.2848 1.1422 0.3245 0.057 Uiso 1 1 calc R U . . .
C20 C 0.4784(9) 0.9162(3) 0.4159(2) 0.0506(15) Uani 1 1 d . . . . .
H17 H 0.4586 0.9230 0.4531 0.061 Uiso 1 1 calc R U . . .
C21 C 0.5098(8) 0.5350(2) 0.3053(2) 0.0432(13) Uani 1 1 d . . . . .
C22 C 0.3945(7) 0.6303(2) 0.2764(2) 0.0412(13) Uani 1 1 d . . . . .
H18 H 0.4113 0.6717 0.2686 0.049 Uiso 1 1 calc R U . . .
C23 C 0.6827(8) 1.1129(3) 0.4027(2) 0.0503(15) Uani 1 1 d . . . . .
H19 H 0.7863 1.1056 0.4218 0.060 Uiso 1 1 calc R U . . .
C24 C 0.4269(9) 0.8627(3) 0.3920(2) 0.0505(16) Uani 1 1 d . . . . .
H20 H 0.3708 0.8325 0.4126 0.061 Uiso 1 1 calc R U . . .
C25 C 0.4256(8) 1.0766(3) 0.3615(3) 0.0479(15) Uani 1 1 d . . . . .
H21 H 0.3520 1.0441 0.3525 0.057 Uiso 1 1 calc R U . . .
C26 C -0.0005(9) 0.9558(3) 0.4372(3) 0.0560(16) Uani 1 1 d . . . . .
C27 C 0.5883(8) 0.9504(3) 0.3317(2) 0.0442(14) Uani 1 1 d . . . . .
H22 H 0.6448 0.9805 0.3112 0.053 Uiso 1 1 calc R U . . .
C28 C 0.6405(8) 1.1709(3) 0.3860(2) 0.0474(14) Uani 1 1 d . . . . .
H23 H 0.7150 1.2036 0.3941 0.057 Uiso 1 1 calc R U . . .
C29 C -0.0269(10) 0.8949(3) 0.4277(3) 0.0578(17) Uani 1 1 d . . . . .
H24 H -0.0518 0.8689 0.4570 0.069 Uiso 1 1 calc R U . . .
C30 C 0.0362(8) 0.9925(3) 0.3939(3) 0.0538(16) Uani 1 1 d . . . . .
H25 H 0.0578 1.0340 0.4001 0.065 Uiso 1 1 calc R U . . .
C31 C 0.6631(10) 0.4973(3) 0.3218(4) 0.073(2) Uani 1 1 d . . . . .
H26 H 0.6246 0.4642 0.3448 0.109 Uiso 1 1 calc R U . . .
H27 H 0.7450 0.5224 0.3415 0.109 Uiso 1 1 calc R U . . .
H28 H 0.7187 0.4809 0.2896 0.109 Uiso 1 1 calc R U . . .
C32 C 0.2201(10) 0.6807(3) 0.4088(3) 0.066(2) Uani 1 1 d . . . . .
H29 H 0.2035 0.6427 0.3880 0.079 Uiso 1 1 calc R U . . .
C33 C 0.1091(11) 0.6780(4) 0.4573(3) 0.076(2) Uani 1 1 d . . . . .
H30 H 0.1495 0.6443 0.4801 0.092 Uiso 1 1 calc R U . . .
H31 H 0.1260 0.7156 0.4780 0.092 Uiso 1 1 calc R U . . .
C34 C -0.0775(12) 0.6701(5) 0.4479(3) 0.087(3) Uani 1 1 d . . . . .
H32 H -0.1192 0.7042 0.4259 0.105 Uiso 1 1 calc R U . . .
H33 H -0.1374 0.6719 0.4830 0.105 Uiso 1 1 calc R U . . .
C35 C 0.4125(11) 0.6877(4) 0.4206(3) 0.079(2) Uani 1 1 d . . . . .
H34 H 0.4750 0.6934 0.3868 0.119 Uiso 1 1 calc R U . . .
H35 H 0.4549 0.6515 0.4387 0.119 Uiso 1 1 calc R U . . .
H36 H 0.4305 0.7228 0.4438 0.119 Uiso 1 1 calc R U . . .
C36 C -0.0190(14) 0.9802(4) 0.4938(3) 0.091(3) Uani 1 1 d . . . . .
H37 H 0.0483 1.0173 0.4973 0.137 Uiso 1 1 calc R U . . .
H38 H 0.0230 0.9503 0.5196 0.137 Uiso 1 1 calc R U . . .
H39 H -0.1402 0.9889 0.5011 0.137 Uiso 1 1 calc R U . . .
C37 C -0.1263(16) 0.6127(5) 0.4205(4) 0.108(3) Uani 1 1 d . . . . .
H40 H -0.0552 0.6073 0.3883 0.162 Uiso 1 1 calc R U . . .
H41 H -0.2476 0.6143 0.4101 0.162 Uiso 1 1 calc R U . . .
H42 H -0.1078 0.5788 0.4450 0.162 Uiso 1 1 calc R U . . .
C38 C -0.169(5) 0.7786(17) 0.0382(15) 0.183(13) Uiso 0.5 1 d . . P A 2
O11 O -0.1850(10) 0.7938(4) 0.1027(2) 0.126(3) Uani 1 1 d . . . . .
C39 C -0.157(5) 0.8678(17) 0.0385(15) 0.085(10) Uiso 0.25 1 d . . P A 1
C40 C 0.126(6) 0.9094(18) 0.0452(17) 0.199(15) Uiso 0.5 1 d . . P . .
C41 C -0.399(3) 0.8842(9) 0.0952(8) 0.094(5) Uiso 0.5 1 d . . P . .
C42 C -0.021(6) 0.8650(19) 0.0387(17) 0.101(12) Uiso 0.25 1 d . . P A 1
C43 C 0.047(6) 0.6679(19) -0.0194(17) 0.203(15) Uiso 0.5 1 d . . P B 2
C44 C -0.048(4) 0.9529(13) 0.0597(11) 0.058(7) Uiso 0.25 1 d . . P A 2
C45 C -0.204(3) 0.8713(11) 0.0931(10) 0.116(7) Uiso 0.5 1 d . . P A .
C46 C -0.112(4) 0.6796(14) -0.0612(12) 0.150(10) Uiso 0.5 1 d . . P B 2
C47 C 0.136(6) 0.740(2) -0.005(2) 0.232(18) Uiso 0.5 1 d . . P B 2
C48 C -0.100(5) 0.9070(16) 0.0769(13) 0.075(9) Uiso 0.25 1 d . . P A 2
C49 C -0.107(3) 0.6803(9) 0.0334(8) 0.092(5) Uiso 0.5 1 d . . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.265(7) . ?
O2 C3 1.362(6) . ?
O2 C9 1.437(6) . ?
O3 C3 1.194(6) . ?
O4 C1 1.360(6) . ?
O4 C2 1.448(6) . ?
O5 C1 1.209(7) . ?
O6 C11 1.229(6) . ?
O7 C10 1.387(6) . ?
O7 C14 1.392(7) . ?
O8 C32 1.441(7) . ?
O9 C6 1.262(8) . ?
N1 C5 1.467(7) . ?
O10 C6 1.235(8) . ?
C1 C7 1.470(8) . ?
C2 C9 1.532(7) . ?
C2 C11 1.535(8) . ?
C3 C15 1.481(8) . ?
C4 C12 1.388(8) . ?
C4 C7 1.399(7) . ?
C5 C16 1.368(8) . ?
C5 C24 1.381(8) . ?
N2 C8 1.480(7) . ?
C6 C9 1.530(8) . ?
C7 C22 1.380(8) . ?
C8 C28 1.346(9) . ?
C8 C19 1.370(8) . ?
C10 C25 1.369(8) . ?
C10 C23 1.382(8) . ?
C12 C21 1.367(9) . ?
C13 C30 1.362(9) . ?
C13 C15 1.398(8) . ?
C14 C27 1.363(8) . ?
C14 C20 1.370(8) . ?
C15 C18 1.385(8) . ?
C16 C27 1.388(8) . ?
C17 C22 1.388(8) . ?
C17 C21 1.396(8) . ?
C18 C29 1.368(8) . ?
C19 C25 1.390(8) . ?
C20 C24 1.389(9) . ?
C21 C31 1.514(9) . ?
C23 C28 1.394(8) . ?
C26 C30 1.381(10) . ?
C26 C29 1.388(9) . ?
C26 C36 1.519(9) . ?
C32 C33 1.487(11) . ?
C32 C35 1.534(12) . ?
C33 C34 1.482(13) . ?
C34 C37 1.498(13) . ?
C38 O11 1.65(4) . ?
C38 C47 1.78(6) 3_465 ?
O11 C45 1.75(3) . ?
C39 C42 1.06(5) . ?
C39 C45 1.41(4) . ?
C40 C42 1.52(5) . ?
C40 C44 1.70(5) . ?
C40 C48 1.93(6) . ?
C41 C45 1.55(3) . ?
C42 C45 1.97(5) . ?
C43 C46 1.64(5) . ?
C43 C47 1.78(6) . ?
C43 C49 1.80(5) . ?
C44 C48 1.18(4) . ?
C45 C48 1.20(4) . ?
C47 C38 1.78(6) 3_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 C9 115.1(4) . . ?
C1 O4 C2 112.8(4) . . ?
C10 O7 C14 119.0(4) . . ?
O5 C1 O4 121.8(5) . . ?
O5 C1 C7 124.7(4) . . ?
O4 C1 C7 113.5(5) . . ?
O4 C2 C9 108.3(4) . . ?
O4 C2 C11 111.4(4) . . ?
C9 C2 C11 109.9(4) . . ?
O3 C3 O2 122.7(5) . . ?
O3 C3 C15 125.9(5) . . ?
O2 C3 C15 111.3(4) . . ?
C12 C4 C7 119.4(5) . . ?
C16 C5 C24 121.0(5) . . ?
C16 C5 N1 119.5(5) . . ?
C24 C5 N1 119.5(5) . . ?
O10 C6 O9 126.5(6) . . ?
O10 C6 C9 118.9(6) . . ?
O9 C6 C9 114.4(6) . . ?
C22 C7 C4 118.7(5) . . ?
C22 C7 C1 123.2(4) . . ?
C4 C7 C1 118.1(5) . . ?
C28 C8 C19 121.9(5) . . ?
C28 C8 N2 120.0(5) . . ?
C19 C8 N2 118.1(5) . . ?
O2 C9 C6 112.7(5) . . ?
O2 C9 C2 107.0(4) . . ?
C6 C9 C2 111.9(4) . . ?
C25 C10 C23 120.6(5) . . ?
C25 C10 O7 123.1(5) . . ?
C23 C10 O7 116.3(5) . . ?
O6 C11 O1 126.8(5) . . ?
O6 C11 C2 120.4(5) . . ?
O1 C11 C2 112.8(5) . . ?
C21 C12 C4 122.1(5) . . ?
C30 C13 C15 119.4(6) . . ?
C27 C14 C20 121.7(6) . . ?
C27 C14 O7 121.8(5) . . ?
C20 C14 O7 116.4(5) . . ?
C18 C15 C13 119.3(5) . . ?
C18 C15 C3 121.6(5) . . ?
C13 C15 C3 119.0(5) . . ?
C5 C16 C27 119.5(5) . . ?
C22 C17 C21 120.0(6) . . ?
C29 C18 C15 120.2(5) . . ?
C8 C19 C25 118.8(6) . . ?
C14 C20 C24 119.1(6) . . ?
C12 C21 C17 118.6(5) . . ?
C12 C21 C31 122.0(5) . . ?
C17 C21 C31 119.5(6) . . ?
C7 C22 C17 121.2(5) . . ?
C10 C23 C28 118.8(5) . . ?
C5 C24 C20 119.2(5) . . ?
C10 C25 C19 119.9(6) . . ?
C30 C26 C29 118.3(6) . . ?
C30 C26 C36 122.1(6) . . ?
C29 C26 C36 119.5(7) . . ?
C14 C27 C16 119.4(5) . . ?
C8 C28 C23 119.9(6) . . ?
C18 C29 C26 120.9(6) . . ?
C13 C30 C26 121.8(6) . . ?
O8 C32 C33 111.1(6) . . ?
O8 C32 C35 106.6(6) . . ?
C33 C32 C35 114.6(7) . . ?
C34 C33 C32 116.5(7) . . ?
C33 C34 C37 114.9(9) . . ?
O11 C38 C47 116(3) . 3_465 ?
C38 O11 C45 94.4(16) . . ?
C42 C39 C45 105(4) . . ?
C44 C40 C48 37.2(16) . . ?
C39 C42 C40 136(5) . . ?
C39 C42 C45 44(3) . . ?
C40 C42 C45 115(3) . . ?
C46 C43 C47 106(3) . . ?
C46 C43 C49 86(2) . . ?
C47 C43 C49 88(3) . . ?
C48 C44 C40 82(3) . . ?
C48 C45 C41 123(3) . . ?
C39 C45 C41 107(3) . . ?
C48 C45 O11 130(2) . . ?
C39 C45 O11 93(2) . . ?
C41 C45 O11 105.1(17) . . ?
C39 C45 C42 31.3(19) . . ?
C41 C45 C42 138(2) . . ?
O11 C45 C42 87.9(17) . . ?
C38 C47 C43 91(3) 3_565 . ?
C44 C48 C45 158(4) . . ?
C44 C48 C40 61(2) . . ?
C45 C48 C40 140(3) . . ?

_refine_diff_density_max         0.689
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.096

_shelxl_version_number           2013-4

