# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Prof. Valeria Nurchi'
_publ_contact_author_email       nurchi@unica.it

_publ_section_title              
;
KOJIC ACID DERIVATIVES AS POWERFUL
CHELATORS FOR IRON(III) AND ALUMINIUM(III).
;
loop_
_publ_author_name
V.Nurchi
G.Crisponi
J.Lachowicz
S.Murgia
M.Arca
A.Pintus
;
P.Gans
;
J.Niclos-Gutierrez
A.Dominguez-Martin
A.Castineiras
M.Remelli
;
Z.Szewczuk
;
T.Lis

# Attachment '- comp_2.cif'

data_08jnac425
_database_code_depnum_ccdc_archive 'CCDC 801244'
#TrackingRef '- comp_2.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 O10, 0.5(H2 O)'
_chemical_formula_sum            'C20 H19 O10.50'
_chemical_formula_weight         427.35

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_Int_Tables_number      15

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

_cell_length_a                   33.2374(10)
_cell_length_b                   7.4001(3)
_cell_length_c                   15.2959(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.956(2)
_cell_angle_gamma                90.00
_cell_volume                     3753.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1935
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      26.405

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1784
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9214
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 KappaAPEXII'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            43337
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         26.02
_reflns_number_total             3649
_reflns_number_gt                3263
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 Software (Bruker, 2005)'
_computing_cell_refinement       'APEX2 Software (Bruker, 2005)'
_computing_data_reduction        'APEX2 Software (Bruker, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2004)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0394P)^2^+4.3401P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3649
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O12 O 0.15116(3) 0.17376(13) 0.26762(6) 0.0170(2) Uani 1 1 d . . .
H12 H 0.1669 0.1948 0.3183 0.020 Uiso 1 1 d R . .
O13 O 0.21137(3) -0.03124(13) 0.33709(6) 0.0191(2) Uani 1 1 d . . .
O22 O 0.11636(3) 0.20103(12) -0.06652(6) 0.0155(2) Uani 1 1 d . . .
O25 O 0.17833(3) 0.67095(13) -0.08417(6) 0.0200(2) Uani 1 1 d . . .
O26 O 0.16728(3) 0.52741(13) 0.07558(6) 0.0213(2) Uani 1 1 d . . .
H26 H 0.1780 0.6295 0.0594 0.026 Uiso 1 1 d R . .
O27 O 0.05314(3) 0.20059(14) -0.20456(7) 0.0216(2) Uani 1 1 d . . .
H27 H 0.0443 0.0956 -0.1864 0.026 Uiso 1 1 d R . .
O32 O 0.08872(3) -0.07411(12) 0.05234(6) 0.0161(2) Uani 1 1 d . . .
O35 O -0.01432(3) 0.10338(14) 0.15178(6) 0.0217(2) Uani 1 1 d . . .
O36 O 0.05380(3) 0.32207(13) 0.15988(7) 0.0229(2) Uani 1 1 d . . .
H36 H 0.0298 0.3465 0.1859 0.028 Uiso 1 1 d R . .
O37A O 0.02951(6) -0.4285(3) -0.04229(14) 0.0342(6) Uani 0.564(3) 1 d P . .
H371 H 0.0220 -0.3514 -0.0935 0.041 Uiso 0.564(3) 1 d PR . .
O37B O 0.07498(7) -0.3388(3) -0.07959(16) 0.0272(7) Uani 0.436(3) 1 d P . .
H372 H 0.0572 -0.2736 -0.1150 0.033 Uiso 0.436(3) 1 d PR . .
C1 C 0.12681(4) 0.19333(17) 0.09216(8) 0.0135(3) Uani 1 1 d . . .
H1 H 0.1238 0.2884 0.1352 0.016 Uiso 1 1 d R . .
C11 C 0.16302(4) 0.07821(17) 0.12417(8) 0.0127(3) Uani 1 1 d . . .
C12 C 0.17337(4) 0.07406(17) 0.21395(8) 0.0133(3) Uani 1 1 d . . .
C13 C 0.20564(4) -0.03408(17) 0.24751(8) 0.0146(3) Uani 1 1 d . . .
C14 C 0.22864(4) -0.12905(18) 0.19113(9) 0.0160(3) Uani 1 1 d . . .
H14 H 0.2516 -0.1992 0.2142 0.019 Uiso 1 1 d R . .
C15 C 0.21899(4) -0.11904(18) 0.10088(9) 0.0168(3) Uani 1 1 d . . .
H15 H 0.2362 -0.1794 0.0625 0.020 Uiso 1 1 d R . .
C16 C 0.18620(4) -0.01942(18) 0.06768(8) 0.0152(3) Uani 1 1 d . . .
H16 H 0.1796 -0.0164 0.0040 0.018 Uiso 1 1 d R . .
C21 C 0.13317(4) 0.28492(18) 0.00655(8) 0.0137(3) Uani 1 1 d . . .
C23 C 0.11948(4) 0.27899(18) -0.14633(8) 0.0156(3) Uani 1 1 d . . .
C24 C 0.14073(4) 0.43123(19) -0.15682(8) 0.0168(3) Uani 1 1 d . . .
H24 H 0.1409 0.4838 -0.2137 0.020 Uiso 1 1 d R . .
C25 C 0.15938(4) 0.52524(18) -0.08253(9) 0.0159(3) Uani 1 1 d . . .
C26 C 0.15338(4) 0.44160(18) 0.00100(8) 0.0150(3) Uani 1 1 d . . .
C27 C 0.09499(4) 0.1799(2) -0.21674(9) 0.0190(3) Uani 1 1 d . . .
H27A H 0.1018 0.0517 -0.2156 0.023 Uiso 1 1 d R . .
H27B H 0.1014 0.2335 -0.2727 0.023 Uiso 1 1 d R . .
C31 C 0.08747(4) 0.09174(18) 0.09096(8) 0.0140(3) Uani 1 1 d . . .
C33 C 0.05530(4) -0.17923(18) 0.04694(9) 0.0174(3) Uani 1 1 d . . .
C34 C 0.02072(4) -0.12758(19) 0.08028(9) 0.0181(3) Uani 1 1 d . . .
H34 H -0.0010 -0.2072 0.0749 0.022 Uiso 1 1 d R . .
C35 C 0.01729(4) 0.04492(19) 0.12128(8) 0.0168(3) Uani 1 1 d . . .
C36 C 0.05357(4) 0.15474(18) 0.12443(8) 0.0161(3) Uani 1 1 d . . .
C37 C 0.06260(5) -0.3544(2) 0.00115(10) 0.0256(3) Uani 1 1 d . . .
H37A H 0.0783 -0.4376 0.0416 0.031 Uiso 1 1 d R . .
H37B H 0.0825 -0.3343 -0.0408 0.031 Uiso 0.50 1 d PR . .
H37C H 0.0373 -0.4251 -0.0022 0.031 Uiso 0.50 1 d PR . .
C130 C 0.24195(5) -0.1487(2) 0.37528(10) 0.0274(3) Uani 1 1 d . . .
H13A H 0.2335 -0.2787 0.3620 0.033 Uiso 1 1 d R . .
H13B H 0.2432 -0.1325 0.4375 0.033 Uiso 1 1 d R . .
H13C H 0.2681 -0.1183 0.3572 0.033 Uiso 1 1 d R . .
O1 O 0.0000 0.50999(19) 0.2500 0.0227(3) Uani 1 2 d S . .
H1A H 0.0191 0.5875 0.2732 0.027 Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O12 0.0175(5) 0.0199(5) 0.0136(4) -0.0031(4) -0.0002(4) 0.0054(4)
O13 0.0217(5) 0.0211(5) 0.0141(4) -0.0005(4) -0.0029(4) 0.0073(4)
O22 0.0181(5) 0.0152(5) 0.0131(4) -0.0002(4) 0.0010(4) -0.0025(4)
O25 0.0222(5) 0.0177(5) 0.0198(5) 0.0035(4) -0.0013(4) -0.0057(4)
O26 0.0278(6) 0.0193(5) 0.0162(5) 0.0008(4) -0.0035(4) -0.0099(4)
O27 0.0166(5) 0.0216(5) 0.0264(5) -0.0009(4) 0.0001(4) -0.0020(4)
O32 0.0141(5) 0.0137(5) 0.0204(5) -0.0011(4) 0.0011(4) 0.0000(4)
O35 0.0154(5) 0.0273(6) 0.0228(5) -0.0031(4) 0.0037(4) 0.0005(4)
O36 0.0184(5) 0.0203(5) 0.0309(6) -0.0074(4) 0.0083(4) 0.0001(4)
O37A 0.0261(11) 0.0260(11) 0.0490(13) -0.0124(9) -0.0087(9) 0.0000(8)
O37B 0.0274(14) 0.0276(14) 0.0267(13) -0.0048(10) 0.0020(10) 0.0076(10)
C1 0.0139(6) 0.0133(6) 0.0131(6) -0.0001(5) 0.0012(5) 0.0004(5)
C11 0.0116(6) 0.0105(6) 0.0160(6) 0.0010(5) 0.0006(5) -0.0031(5)
C12 0.0133(6) 0.0115(6) 0.0154(6) -0.0013(5) 0.0030(5) -0.0017(5)
C13 0.0155(6) 0.0130(6) 0.0149(6) -0.0002(5) -0.0007(5) -0.0022(5)
C14 0.0130(6) 0.0138(6) 0.0212(7) -0.0008(5) 0.0000(5) 0.0006(5)
C15 0.0153(6) 0.0151(7) 0.0204(7) -0.0038(5) 0.0048(5) -0.0008(5)
C16 0.0166(7) 0.0146(6) 0.0145(6) -0.0007(5) 0.0020(5) -0.0037(5)
C21 0.0127(6) 0.0150(6) 0.0133(6) -0.0002(5) -0.0001(5) 0.0023(5)
C23 0.0158(6) 0.0176(7) 0.0136(6) 0.0012(5) 0.0023(5) 0.0025(5)
C24 0.0176(7) 0.0192(7) 0.0137(6) 0.0025(5) 0.0008(5) -0.0004(5)
C25 0.0132(6) 0.0160(7) 0.0185(6) 0.0023(5) 0.0010(5) 0.0011(5)
C26 0.0140(6) 0.0156(7) 0.0149(6) 0.0003(5) -0.0018(5) 0.0007(5)
C27 0.0184(7) 0.0223(7) 0.0165(7) -0.0017(5) 0.0023(5) -0.0025(6)
C31 0.0165(7) 0.0139(6) 0.0114(6) 0.0021(5) -0.0004(5) 0.0007(5)
C33 0.0161(7) 0.0164(7) 0.0192(7) 0.0029(5) -0.0026(5) -0.0014(5)
C34 0.0162(7) 0.0199(7) 0.0180(6) 0.0023(5) -0.0013(5) -0.0030(5)
C35 0.0156(7) 0.0225(7) 0.0121(6) 0.0037(5) -0.0002(5) 0.0009(5)
C36 0.0180(7) 0.0163(7) 0.0140(6) 0.0014(5) 0.0008(5) 0.0014(5)
C37 0.0230(8) 0.0194(7) 0.0341(8) -0.0048(6) -0.0005(6) 0.0004(6)
C130 0.0287(8) 0.0330(9) 0.0195(7) 0.0002(6) -0.0057(6) 0.0141(7)
O1 0.0198(7) 0.0188(7) 0.0299(8) 0.000 0.0060(6) 0.000

_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
O12 C12 1.3591(16) . ?
O12 H12 0.9184 . ?
O13 C13 1.3705(15) . ?
O13 C130 1.4310(17) . ?
O22 C23 1.3607(15) . ?
O22 C21 1.3640(15) . ?
O25 C25 1.2498(17) . ?
O26 C26 1.3584(16) . ?
O26 H26 0.8785 . ?
O27 C27 1.4243(17) . ?
O27 H27 0.8823 . ?
O32 C33 1.3539(16) . ?
O32 C31 1.3640(16) . ?
O35 C35 1.2554(17) . ?
O36 C36 1.3516(16) . ?
O36 H36 0.9335 . ?
O37A C37 1.360(2) . ?
O37A H371 0.9873 . ?
O37B H372 0.9109 . ?
C1 C21 1.5023(17) . ?
C1 C31 1.5073(18) . ?
C1 C11 1.5273(17) . ?
C1 H1 0.9729 . ?
C11 C12 1.3927(18) . ?
C11 C16 1.3977(18) . ?
C12 C13 1.4066(18) . ?
C13 C14 1.3831(19) . ?
C14 C15 1.3975(19) . ?
C14 H14 0.9690 . ?
C15 C16 1.3831(19) . ?
C15 H15 0.9579 . ?
C16 H16 0.9843 . ?
C21 C26 1.3455(19) . ?
C23 C24 1.3451(19) . ?
C23 C27 1.4964(18) . ?
C24 C25 1.4361(19) . ?
C24 H24 0.9537 . ?
C25 C26 1.4459(18) . ?
C27 H27A 0.9748 . ?
C27 H27B 0.9793 . ?
C31 C36 1.3524(19) . ?
C33 C34 1.345(2) . ?
C33 C37 1.501(2) . ?
C34 C35 1.430(2) . ?
C34 H34 0.9302 . ?
C35 C36 1.4522(19) . ?
C37 H37A 0.9955 . ?
C37 H37B 0.9642 . ?
C37 H37C 0.9900 . ?
C130 H13A 1.0183 . ?
C130 H13B 0.9571 . ?
C130 H13C 0.9576 . ?
O1 H1A 0.9094 . ?

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
C12 O12 H12 107.5 . . ?
C13 O13 C130 116.40(10) . . ?
C23 O22 C21 119.33(10) . . ?
C26 O26 H26 106.7 . . ?
C27 O27 H27 107.2 . . ?
C33 O32 C31 119.61(10) . . ?
C36 O36 H36 111.5 . . ?
C37 O37A H371 107.8 . . ?
C21 C1 C31 112.86(10) . . ?
C21 C1 C11 112.09(10) . . ?
C31 C1 C11 112.92(10) . . ?
C21 C1 H1 106.9 . . ?
C31 C1 H1 103.8 . . ?
C11 C1 H1 107.6 . . ?
C12 C11 C16 119.27(12) . . ?
C12 C11 C1 117.64(11) . . ?
C16 C11 C1 123.08(11) . . ?
O12 C12 C11 118.43(11) . . ?
O12 C12 C13 121.38(11) . . ?
C11 C12 C13 120.18(12) . . ?
O13 C13 C14 125.92(12) . . ?
O13 C13 C12 113.97(11) . . ?
C14 C13 C12 120.11(12) . . ?
C13 C14 C15 119.35(12) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 120.80(12) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 118.3 . . ?
C15 C16 C11 120.17(12) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 120.3 . . ?
C26 C21 O22 121.24(12) . . ?
C26 C21 C1 122.99(12) . . ?
O22 C21 C1 115.76(11) . . ?
C24 C23 O22 122.36(12) . . ?
C24 C23 C27 126.06(12) . . ?
O22 C23 C27 111.51(11) . . ?
C23 C24 C25 120.87(12) . . ?
C23 C24 H24 119.1 . . ?
C25 C24 H24 119.7 . . ?
O25 C25 C24 126.36(12) . . ?
O25 C25 C26 119.17(12) . . ?
C24 C25 C26 114.41(12) . . ?
C21 C26 O26 119.48(12) . . ?
C21 C26 C25 121.64(12) . . ?
O26 C26 C25 118.84(12) . . ?
O27 C27 C23 109.92(11) . . ?
O27 C27 H27A 109.2 . . ?
C23 C27 H27A 110.5 . . ?
O27 C27 H27B 110.0 . . ?
C23 C27 H27B 106.9 . . ?
H27A C27 H27B 110.3 . . ?
C36 C31 O32 121.68(12) . . ?
C36 C31 C1 124.63(12) . . ?
O32 C31 C1 113.69(11) . . ?
C34 C33 O32 122.19(13) . . ?
C34 C33 C37 126.32(13) . . ?
O32 C33 C37 111.49(12) . . ?
C33 C34 C35 121.07(13) . . ?
C33 C34 H34 117.6 . . ?
C35 C34 H34 121.3 . . ?
O35 C35 C34 124.37(13) . . ?
O35 C35 C36 120.60(13) . . ?
C34 C35 C36 115.02(12) . . ?
O36 C36 C31 119.06(12) . . ?
O36 C36 C35 120.52(12) . . ?
C31 C36 C35 120.41(12) . . ?
O37A C37 C33 115.14(14) . . ?
O37A C37 H37A 115.3 . . ?
C33 C37 H37A 109.8 . . ?
O37A C37 H37B 107.8 . . ?
C33 C37 H37B 108.5 . . ?
H37A C37 H37B 98.9 . . ?
O37A C37 H37C 26.6 . . ?
C33 C37 H37C 108.4 . . ?
H37A C37 H37C 96.5 . . ?
H37B C37 H37C 131.9 . . ?
O13 C130 H13A 108.3 . . ?
O13 C130 H13B 108.1 . . ?
H13A C130 H13B 108.0 . . ?
O13 C130 H13C 111.9 . . ?
H13A C130 H13C 114.0 . . ?
H13B C130 H13C 106.2 . . ?

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
C21 C1 C11 C12 142.92(12) . . . . ?
C31 C1 C11 C12 -88.26(14) . . . . ?
C21 C1 C11 C16 -36.09(17) . . . . ?
C31 C1 C11 C16 92.73(14) . . . . ?
C16 C11 C12 O12 178.23(11) . . . . ?
C1 C11 C12 O12 -0.82(17) . . . . ?
C16 C11 C12 C13 -2.97(19) . . . . ?
C1 C11 C12 C13 177.99(11) . . . . ?
C130 O13 C13 C14 -5.3(2) . . . . ?
C130 O13 C13 C12 175.70(12) . . . . ?
O12 C12 C13 O13 1.42(18) . . . . ?
C11 C12 C13 O13 -177.35(11) . . . . ?
O12 C12 C13 C14 -177.68(12) . . . . ?
C11 C12 C13 C14 3.55(19) . . . . ?
O13 C13 C14 C15 179.82(12) . . . . ?
C12 C13 C14 C15 -1.2(2) . . . . ?
C13 C14 C15 C16 -1.7(2) . . . . ?
C14 C15 C16 C11 2.3(2) . . . . ?
C12 C11 C16 C15 0.07(19) . . . . ?
C1 C11 C16 C15 179.06(12) . . . . ?
C23 O22 C21 C26 -1.18(18) . . . . ?
C23 O22 C21 C1 177.56(11) . . . . ?
C31 C1 C21 C26 147.77(13) . . . . ?
C11 C1 C21 C26 -83.38(15) . . . . ?
C31 C1 C21 O22 -30.95(15) . . . . ?
C11 C1 C21 O22 97.90(13) . . . . ?
C21 O22 C23 C24 4.14(18) . . . . ?
C21 O22 C23 C27 -172.92(11) . . . . ?
O22 C23 C24 C25 -3.7(2) . . . . ?
C27 C23 C24 C25 172.92(13) . . . . ?
C23 C24 C25 O25 -176.88(13) . . . . ?
C23 C24 C25 C26 0.41(19) . . . . ?
O22 C21 C26 O26 175.46(11) . . . . ?
C1 C21 C26 O26 -3.2(2) . . . . ?
O22 C21 C26 C25 -2.1(2) . . . . ?
C1 C21 C26 C25 179.26(12) . . . . ?
O25 C25 C26 C21 179.92(13) . . . . ?
C24 C25 C26 C21 2.42(19) . . . . ?
O25 C25 C26 O26 2.36(19) . . . . ?
C24 C25 C26 O26 -175.14(12) . . . . ?
C24 C23 C27 O27 -109.24(15) . . . . ?
O22 C23 C27 O27 67.68(14) . . . . ?
C33 O32 C31 C36 0.10(17) . . . . ?
C33 O32 C31 C1 -179.95(11) . . . . ?
C21 C1 C31 C36 -99.46(15) . . . . ?
C11 C1 C31 C36 132.13(13) . . . . ?
C21 C1 C31 O32 80.59(13) . . . . ?
C11 C1 C31 O32 -47.83(14) . . . . ?
C31 O32 C33 C34 -1.50(18) . . . . ?
C31 O32 C33 C37 179.10(11) . . . . ?
O32 C33 C34 C35 1.8(2) . . . . ?
C37 C33 C34 C35 -178.90(13) . . . . ?
C33 C34 C35 O35 178.17(13) . . . . ?
C33 C34 C35 C36 -0.69(18) . . . . ?
O32 C31 C36 O36 -178.27(11) . . . . ?
C1 C31 C36 O36 1.77(19) . . . . ?
O32 C31 C36 C35 0.95(19) . . . . ?
C1 C31 C36 C35 -179.00(12) . . . . ?
O35 C35 C36 O36 -0.33(19) . . . . ?
C34 C35 C36 O36 178.57(11) . . . . ?
O35 C35 C36 C31 -179.55(12) . . . . ?
C34 C35 C36 C31 -0.64(18) . . . . ?
C34 C33 C37 O37A 29.5(2) . . . . ?
O32 C33 C37 O37A -151.17(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O12 H12 O13 0.92 2.24 2.6726(13) 108.3 .
O12 H12 O25 0.92 1.81 2.6445(13) 149.8 6_566
O26 H26 O25 0.88 2.22 2.7126(13) 115.3 .
O27 H27 O35 0.88 1.87 2.7424(14) 167.4 5
O36 H36 O1 0.93 1.88 2.7152(12) 147.4 .
O36 H36 O35 0.93 2.36 2.7788(14) 107.1 .
O37A H371 O35 0.99 2.05 2.955(2) 151.7 5
O37B H372 O35 0.91 1.96 2.831(3) 160.3 5
O1 H1A O27 0.91 1.95 2.8320(15) 163.0 6_566

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.02
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.043

# Attachment '- comp_3.cif'

data_jola0
_database_code_depnum_ccdc_archive 'CCDC 801245'
#TrackingRef '- comp_3.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 O10'
_chemical_formula_sum            'C20 H18 O10'
_chemical_formula_weight         418.34

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   8.365(3)
_cell_length_b                   13.150(4)
_cell_length_c                   16.819(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.44(5)
_cell_angle_gamma                90.00
_cell_volume                     1830.0(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    85(2)
_cell_measurement_reflns_used    5440
_cell_measurement_theta_min      4
_cell_measurement_theta_max      32

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      85(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Xcalibur PX kappa-geometry diffractometer with Onyx CCD camera'
_diffrn_measurement_method       'omega and phi'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15699
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_sigmaI/netI    0.1730
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.81
_diffrn_reflns_theta_max         32.57
_reflns_number_total             6356
_reflns_number_gt                3013
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD; Oxford-Diffraction Poland, 2003'
_computing_cell_refinement       'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_data_reduction        'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.005P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6356
_refine_ls_number_parameters     304
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1626
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.0635
_refine_ls_wR_factor_gt          0.0543
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.65451(19) 0.75779(12) 0.44185(9) 0.0118(4) Uani 1 1 d . . .
H1 H 0.7640 0.7550 0.4248 0.014 Uiso 1 1 calc R . .
C11 C 0.68233(19) 0.77848(11) 0.53213(9) 0.0119(4) Uani 1 1 d . . .
C12 C 0.55394(19) 0.79541(12) 0.57551(10) 0.0133(4) Uani 1 1 d . . .
H12 H 0.4465 0.8003 0.5481 0.016 Uiso 1 1 calc R . .
C13 C 0.58386(19) 0.80490(12) 0.65777(10) 0.0132(4) Uani 1 1 d . . .
O13 O 0.46948(13) 0.82327(8) 0.70677(6) 0.0198(3) Uani 1 1 d . . .
C130 C 0.30567(19) 0.83350(14) 0.66819(10) 0.0248(5) Uani 1 1 d . . .
H131 H 0.2714 0.7703 0.6398 0.037 Uiso 1 1 calc R . .
H132 H 0.2983 0.8899 0.6297 0.037 Uiso 1 1 calc R . .
H133 H 0.2354 0.8472 0.7087 0.037 Uiso 1 1 calc R . .
C14 C 0.7404(2) 0.79667(12) 0.69911(10) 0.0146(4) Uani 1 1 d . . .
O14 O 0.77296(12) 0.80547(9) 0.78109(6) 0.0189(3) Uani 1 1 d . . .
H14 H 0.6859 0.8112 0.8000 0.028 Uiso 1 1 calc R . .
C15 C 0.8670(2) 0.78147(12) 0.65640(10) 0.0165(4) Uani 1 1 d . . .
H15 H 0.9744 0.7772 0.6839 0.020 Uiso 1 1 calc R . .
C16 C 0.8379(2) 0.77233(12) 0.57307(10) 0.0158(4) Uani 1 1 d . . .
H16 H 0.9258 0.7618 0.5441 0.019 Uiso 1 1 calc R . .
C21 C 0.57832(18) 0.65540(13) 0.42234(9) 0.0119(4) Uani 1 1 d . . .
O22 O 0.43003(12) 0.64563(8) 0.44648(6) 0.0129(3) Uani 1 1 d . A .
C23 C 0.34473(18) 0.55894(13) 0.43062(9) 0.0134(4) Uani 1 1 d D . .
C24 C 0.40059(19) 0.47967(12) 0.39288(10) 0.0144(4) Uani 1 1 d . A .
H24 H 0.3385 0.4190 0.3853 0.017 Uiso 1 1 calc R . .
C25 C 0.55388(19) 0.48539(13) 0.36372(10) 0.0144(4) Uani 1 1 d . . .
O25 O 0.61025(13) 0.41686(8) 0.32468(7) 0.0208(3) Uani 1 1 d . A .
C26 C 0.63972(19) 0.57961(13) 0.38260(9) 0.0122(4) Uani 1 1 d . A .
O26 O 0.78696(13) 0.59349(8) 0.35824(7) 0.0182(3) Uani 1 1 d . . .
H26 H 0.8143 0.5400 0.3365 0.027 Uiso 1 1 calc R A .
C27A C 0.1808(13) 0.5698(10) 0.4564(11) 0.0196(8) Uani 0.5638(17) 1 d PD A 1
H27A H 0.1176 0.5065 0.4446 0.024 Uiso 0.5638(17) 1 calc PR A 1
H27B H 0.1920 0.5831 0.5149 0.024 Uiso 0.5638(17) 1 calc PR A 1
O27A O 0.0978(2) 0.65622(15) 0.41098(12) 0.0179(6) Uani 0.5638(17) 1 d PD A 1
H27C H -0.0020 0.6448 0.4020 0.027 Uiso 0.5638(17) 1 calc PR A 1
C27B C 0.1864(17) 0.5633(13) 0.4620(15) 0.0196(8) Uani 0.4362(17) 1 d PD A 2
H27D H 0.2041 0.5890 0.5179 0.024 Uiso 0.4362(17) 1 calc PR A 2
H27E H 0.1135 0.6114 0.4290 0.024 Uiso 0.4362(17) 1 calc PR A 2
O27B O 0.1103(3) 0.46324(19) 0.46009(16) 0.0196(8) Uani 0.4362(17) 1 d PD A 2
H27F H 0.0792 0.4462 0.4122 0.029 Uiso 0.4362(17) 1 calc PR A 2
C31 C 0.55952(18) 0.83529(12) 0.38863(9) 0.0125(4) Uani 1 1 d . . .
O32 O 0.41071(13) 0.85538(8) 0.41005(6) 0.0170(3) Uani 1 1 d . A .
C33 C 0.3021(2) 0.91140(13) 0.36133(10) 0.0177(4) Uani 1 1 d D . .
C34 C 0.33556(19) 0.95111(12) 0.29273(10) 0.0147(4) Uani 1 1 d . A .
H34 H 0.2564 0.9911 0.2606 0.018 Uiso 1 1 calc R . .
C35 C 0.4897(2) 0.93435(12) 0.26650(10) 0.0147(4) Uani 1 1 d . . .
O35 O 0.52598(13) 0.96413(8) 0.20054(7) 0.0203(3) Uani 1 1 d . A .
C36 C 0.6017(2) 0.87528(12) 0.32135(10) 0.0138(4) Uani 1 1 d . A .
O36 O 0.75028(13) 0.85357(9) 0.30085(7) 0.0216(3) Uani 1 1 d . . .
H36 H 0.7616 0.8845 0.2583 0.032 Uiso 1 1 calc R A .
C37A C 0.1523(13) 0.9328(6) 0.3978(8) 0.0238(16) Uani 0.5638(17) 1 d PD A 3
H37A H 0.1574 1.0029 0.4194 0.029 Uiso 0.5638(17) 1 calc PR A 3
H37B H 0.0566 0.9280 0.3556 0.029 Uiso 0.5638(17) 1 calc PR A 3
O37A O 0.1354(2) 0.86237(16) 0.46096(12) 0.0210(6) Uani 0.5638(17) 1 d PD A 3
H37C H 0.1280 0.8030 0.4423 0.032 Uiso 0.5638(17) 1 calc PR A 3
C37B C 0.1360(17) 0.9052(8) 0.3886(12) 0.0238(16) Uani 0.4362(17) 1 d PD A 4
H37D H 0.1469 0.9227 0.4464 0.029 Uiso 0.4362(17) 1 calc PR A 4
H37E H 0.0636 0.9560 0.3585 0.029 Uiso 0.4362(17) 1 calc PR A 4
O37B O 0.0627(3) 0.8049(2) 0.37637(18) 0.0270(9) Uani 0.4362(17) 1 d PD A 4
H37F H -0.0202 0.8086 0.3416 0.040 Uiso 0.4362(17) 1 calc PR A 4

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0118(9) 0.0151(10) 0.0091(9) -0.0001(7) 0.0041(7) 0.0000(8)
C11 0.0163(10) 0.0100(10) 0.0090(9) 0.0016(7) 0.0009(7) -0.0021(8)
C12 0.0131(9) 0.0124(10) 0.0138(10) -0.0005(7) -0.0001(7) 0.0026(8)
C13 0.0146(10) 0.0121(10) 0.0136(10) -0.0014(7) 0.0041(7) -0.0001(8)
O13 0.0173(7) 0.0276(8) 0.0147(7) -0.0026(6) 0.0030(5) 0.0026(6)
C130 0.0138(10) 0.0364(12) 0.0242(11) -0.0052(9) 0.0025(8) 0.0029(9)
C14 0.0213(11) 0.0135(10) 0.0084(9) 0.0006(7) 0.0001(8) -0.0018(8)
O14 0.0186(7) 0.0268(7) 0.0108(7) -0.0016(6) 0.0002(5) -0.0009(6)
C15 0.0124(10) 0.0202(11) 0.0163(10) 0.0021(8) 0.0001(8) -0.0024(8)
C16 0.0136(10) 0.0190(11) 0.0156(10) 0.0000(8) 0.0051(8) -0.0019(8)
C21 0.0087(9) 0.0192(11) 0.0076(9) 0.0030(8) 0.0011(7) -0.0007(8)
O22 0.0107(6) 0.0154(7) 0.0130(6) -0.0018(5) 0.0025(5) -0.0004(5)
C23 0.0117(9) 0.0182(11) 0.0099(9) 0.0017(7) 0.0009(7) -0.0025(8)
C24 0.0165(10) 0.0148(10) 0.0119(10) 0.0000(8) 0.0015(7) -0.0057(8)
C25 0.0156(10) 0.0174(11) 0.0093(10) 0.0008(8) -0.0012(7) -0.0007(8)
O25 0.0243(7) 0.0187(7) 0.0214(7) -0.0072(6) 0.0099(5) -0.0014(6)
C26 0.0103(9) 0.0178(10) 0.0087(9) 0.0018(7) 0.0018(7) 0.0010(8)
O26 0.0163(7) 0.0183(7) 0.0217(8) -0.0064(6) 0.0086(5) -0.0013(6)
C27A 0.0136(11) 0.0240(15) 0.022(2) -0.0059(13) 0.0048(13) -0.0045(11)
O27A 0.0069(11) 0.0228(14) 0.0232(13) 0.0022(10) -0.0009(9) 0.0012(10)
C27B 0.0136(11) 0.0240(15) 0.022(2) -0.0059(13) 0.0048(13) -0.0045(11)
O27B 0.0185(16) 0.0264(19) 0.0141(16) 0.0004(13) 0.0026(12) -0.0032(14)
C31 0.0118(9) 0.0122(10) 0.0131(9) -0.0030(7) 0.0009(7) -0.0002(8)
O32 0.0180(7) 0.0197(7) 0.0138(7) 0.0045(5) 0.0045(5) 0.0073(6)
C33 0.0182(10) 0.0177(11) 0.0167(10) 0.0007(8) 0.0014(8) 0.0056(9)
C34 0.0163(9) 0.0132(10) 0.0133(10) 0.0020(7) -0.0024(7) 0.0030(8)
C35 0.0175(10) 0.0090(10) 0.0165(10) -0.0020(7) -0.0009(8) -0.0045(8)
O35 0.0213(7) 0.0245(7) 0.0147(7) 0.0069(6) 0.0016(5) -0.0053(6)
C36 0.0152(10) 0.0140(10) 0.0118(9) -0.0011(7) 0.0007(7) -0.0019(8)
O36 0.0161(7) 0.0300(8) 0.0197(8) 0.0126(6) 0.0063(5) 0.0025(6)
C37A 0.023(2) 0.019(4) 0.032(3) 0.014(4) 0.015(2) 0.013(3)
O37A 0.0214(13) 0.0230(14) 0.0205(13) 0.0019(10) 0.0092(10) -0.0002(12)
C37B 0.023(2) 0.019(4) 0.032(3) 0.014(4) 0.015(2) 0.013(3)
O37B 0.0167(17) 0.0312(19) 0.032(2) 0.0097(15) 0.0012(13) -0.0014(14)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C31 1.504(2) . ?
C1 C21 1.505(2) . ?
C1 C11 1.526(2) . ?
C1 H1 1.0000 . ?
C11 C16 1.383(2) . ?
C11 C12 1.402(2) . ?
C12 C13 1.375(2) . ?
C12 H12 0.9500 . ?
C13 O13 1.3727(18) . ?
C13 C14 1.394(2) . ?
O13 C130 1.4338(19) . ?
C130 H131 0.9800 . ?
C130 H132 0.9800 . ?
C130 H133 0.9800 . ?
C14 O14 1.3705(18) . ?
C14 C15 1.379(2) . ?
O14 H14 0.8400 . ?
C15 C16 1.392(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.343(2) . ?
C21 O22 1.3667(18) . ?
O22 C23 1.3506(18) . ?
C23 C24 1.340(2) . ?
C23 C27B 1.497(11) . ?
C23 C27A 1.504(9) . ?
C24 C25 1.440(2) . ?
C24 H24 0.9500 . ?
C25 O25 1.2477(17) . ?
C25 C26 1.444(2) . ?
C26 O26 1.3662(18) . ?
O26 H26 0.8400 . ?
C27A O27A 1.484(14) . ?
C27A H27A 0.9900 . ?
C27A H27B 0.9900 . ?
O27A H27C 0.8400 . ?
C27B O27B 1.460(16) . ?
C27B H27D 0.9900 . ?
C27B H27E 0.9900 . ?
O27B H27F 0.8400 . ?
C31 C36 1.341(2) . ?
C31 O32 1.3714(18) . ?
O32 C33 1.3495(19) . ?
C33 C34 1.333(2) . ?
C33 C37A 1.500(8) . ?
C33 C37B 1.528(10) . ?
C34 C35 1.440(2) . ?
C34 H34 0.9500 . ?
C35 O35 1.2550(18) . ?
C35 C36 1.441(2) . ?
C36 O36 1.3682(19) . ?
O36 H36 0.8400 . ?
C37A O37A 1.433(11) . ?
C37A H37A 0.9900 . ?
C37A H37B 0.9900 . ?
O37A H37C 0.8400 . ?
C37B O37B 1.456(10) . ?
C37B H37D 0.9900 . ?
C37B H37E 0.9900 . ?
O37B H37F 0.8400 . ?

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
C31 C1 C21 107.85(13) . . ?
C31 C1 C11 117.47(13) . . ?
C21 C1 C11 111.97(13) . . ?
C31 C1 H1 106.3 . . ?
C21 C1 H1 106.3 . . ?
C11 C1 H1 106.3 . . ?
C16 C11 C12 119.16(16) . . ?
C16 C11 C1 118.68(15) . . ?
C12 C11 C1 121.97(15) . . ?
C13 C12 C11 119.86(16) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
O13 C13 C12 125.45(15) . . ?
O13 C13 C14 113.62(14) . . ?
C12 C13 C14 120.92(16) . . ?
C13 O13 C130 116.67(13) . . ?
O13 C130 H131 109.5 . . ?
O13 C130 H132 109.5 . . ?
H131 C130 H132 109.5 . . ?
O13 C130 H133 109.5 . . ?
H131 C130 H133 109.5 . . ?
H132 C130 H133 109.5 . . ?
O14 C14 C15 118.82(16) . . ?
O14 C14 C13 121.92(15) . . ?
C15 C14 C13 119.25(16) . . ?
C14 O14 H14 109.5 . . ?
C14 C15 C16 120.20(17) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.60(16) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C26 C21 O22 120.54(15) . . ?
C26 C21 C1 126.26(14) . . ?
O22 C21 C1 113.15(14) . . ?
C23 O22 C21 119.80(13) . . ?
C24 C23 O22 122.64(14) . . ?
C24 C23 C27B 125.8(7) . . ?
O22 C23 C27B 111.5(7) . . ?
C24 C23 C27A 127.3(6) . . ?
O22 C23 C27A 109.9(6) . . ?
C23 C24 C25 120.69(16) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
O25 C25 C24 124.44(16) . . ?
O25 C25 C26 121.43(15) . . ?
C24 C25 C26 114.13(15) . . ?
C21 C26 O26 118.52(15) . . ?
C21 C26 C25 122.13(15) . . ?
O26 C26 C25 119.33(14) . . ?
C26 O26 H26 109.5 . . ?
O27A C27A C23 107.5(8) . . ?
O27A C27A H27A 110.2 . . ?
C23 C27A H27A 110.2 . . ?
O27A C27A H27B 110.2 . . ?
C23 C27A H27B 110.2 . . ?
H27A C27A H27B 108.5 . . ?
O27B C27B C23 111.3(11) . . ?
O27B C27B H27D 109.4 . . ?
C23 C27B H27D 109.4 . . ?
O27B C27B H27E 109.4 . . ?
C23 C27B H27E 109.4 . . ?
H27D C27B H27E 108.0 . . ?
C27B O27B H27F 109.5 . . ?
C36 C31 O32 120.48(15) . . ?
C36 C31 C1 125.91(14) . . ?
O32 C31 C1 113.26(13) . . ?
C33 O32 C31 120.13(13) . . ?
C34 C33 O32 122.07(15) . . ?
C34 C33 C37A 125.0(5) . . ?
O32 C33 C37A 112.5(6) . . ?
C34 C33 C37B 126.6(8) . . ?
O32 C33 C37B 110.5(7) . . ?
C33 C34 C35 121.11(16) . . ?
C33 C34 H34 119.4 . . ?
C35 C34 H34 119.4 . . ?
O35 C35 C34 124.52(16) . . ?
O35 C35 C36 121.01(15) . . ?
C34 C35 C36 114.42(16) . . ?
C31 C36 O36 119.47(15) . . ?
C31 C36 C35 121.66(16) . . ?
O36 C36 C35 118.70(15) . . ?
C36 O36 H36 109.5 . . ?
O37A C37A C33 111.2(7) . . ?
O37A C37A H37A 109.4 . . ?
C33 C37A H37A 109.4 . . ?
C33 C37A H37B 109.4 . . ?
H37A C37A H37B 108.0 . . ?
O37B C37B C33 112.9(7) . . ?
O37B C37B H37D 109.0 . . ?
C33 C37B H37D 109.0 . . ?
O37B C37B H37E 109.0 . . ?
C33 C37B H37E 109.0 . . ?
H37D C37B H37E 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C31 C1 C11 C16 -129.11(16) . . . . ?
C21 C1 C11 C16 105.28(17) . . . . ?
C31 C1 C11 C12 56.1(2) . . . . ?
C21 C1 C11 C12 -69.56(19) . . . . ?
C16 C11 C12 C13 -0.5(2) . . . . ?
C1 C11 C12 C13 174.33(14) . . . . ?
C11 C12 C13 O13 178.82(14) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C13 O13 C130 -0.2(2) . . . . ?
C14 C13 O13 C130 179.49(14) . . . . ?
O13 C13 C14 O14 0.6(2) . . . . ?
C12 C13 C14 O14 -179.74(15) . . . . ?
O13 C13 C14 C15 -177.95(14) . . . . ?
C12 C13 C14 C15 1.7(3) . . . . ?
O14 C14 C15 C16 -179.93(14) . . . . ?
C13 C14 C15 C16 -1.3(3) . . . . ?
C12 C11 C16 C15 0.8(2) . . . . ?
C1 C11 C16 C15 -174.14(14) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
C31 C1 C21 C26 107.63(18) . . . . ?
C11 C1 C21 C26 -121.64(18) . . . . ?
C31 C1 C21 O22 -69.73(16) . . . . ?
C11 C1 C21 O22 61.00(18) . . . . ?
C26 C21 O22 C23 0.3(2) . . . . ?
C1 C21 O22 C23 177.83(13) . . . . ?
C21 O22 C23 C24 1.3(2) . . . . ?
C21 O22 C23 C27B 179.9(10) . . . . ?
C21 O22 C23 C27A -175.1(7) . . . . ?
O22 C23 C24 C25 -2.9(3) . . . . ?
C27B C23 C24 C25 178.6(11) . . . . ?
C27A C23 C24 C25 172.7(8) . . . . ?
C23 C24 C25 O25 -176.34(16) . . . . ?
C23 C24 C25 C26 2.9(2) . . . . ?
O22 C21 C26 O26 178.73(14) . . . . ?
C1 C21 C26 O26 1.5(3) . . . . ?
O22 C21 C26 C25 -0.1(2) . . . . ?
C1 C21 C26 C25 -177.27(15) . . . . ?
O25 C25 C26 C21 177.82(16) . . . . ?
C24 C25 C26 C21 -1.5(2) . . . . ?
O25 C25 C26 O26 -1.0(2) . . . . ?
C24 C25 C26 O26 179.74(14) . . . . ?
C24 C23 C27A O27A -116.5(7) . . . . ?
O22 C23 C27A O27A 59.6(11) . . . . ?
C24 C23 C27B O27B 11(2) . . . . ?
O22 C23 C27B O27B -168.0(10) . . . . ?
C21 C1 C31 C36 -100.64(18) . . . . ?
C11 C1 C31 C36 131.74(17) . . . . ?
C21 C1 C31 O32 72.49(16) . . . . ?
C11 C1 C31 O32 -55.13(19) . . . . ?
C36 C31 O32 C33 3.4(2) . . . . ?
C1 C31 O32 C33 -170.10(13) . . . . ?
C31 O32 C33 C34 -1.8(2) . . . . ?
C31 O32 C33 C37A -175.1(4) . . . . ?
C31 O32 C33 C37B 168.3(5) . . . . ?
O32 C33 C34 C35 1.1(2) . . . . ?
C37A C33 C34 C35 173.6(5) . . . . ?
C37B C33 C34 C35 -167.3(6) . . . . ?
C33 C34 C35 O35 175.53(16) . . . . ?
C33 C34 C35 C36 -1.9(2) . . . . ?
O32 C31 C36 O36 -179.50(14) . . . . ?
C1 C31 C36 O36 -6.8(2) . . . . ?
O32 C31 C36 C35 -4.4(2) . . . . ?
C1 C31 C36 C35 168.25(15) . . . . ?
O35 C35 C36 C31 -173.97(15) . . . . ?
C34 C35 C36 C31 3.6(2) . . . . ?
O35 C35 C36 O36 1.1(2) . . . . ?
C34 C35 C36 O36 178.68(14) . . . . ?
C34 C33 C37A O37A 167.1(4) . . . . ?
O32 C33 C37A O37A -19.8(8) . . . . ?
C34 C33 C37B O37B 100.8(11) . . . . ?
O32 C33 C37B O37B -68.8(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O14 H14 O13 0.84 2.22 2.670(2) 113.7 .
O14 H14 O27A 0.84 2.15 2.848(2) 140.7 4_676
O14 H14 O37B 0.84 2.33 2.932(3) 128.9 4_676
O26 H26 O25 0.84 2.34 2.767(2) 112.0 .
O26 H26 O35 0.84 1.85 2.603(2) 148.8 2_645
O36 H36 O35 0.84 2.32 2.748(2) 112.4 .
O36 H36 O25 0.84 1.93 2.690(2) 150.1 2_655
O27A H27C O26 0.84 1.93 2.748(2) 163.7 1_455
O27B H27F O35 0.84 1.98 2.774(3) 156.4 2_545
O37B H37F O36 0.84 2.03 2.807(3) 153.5 1_455
O37A H37C O27A 0.84 2.01 2.842(3) 172.3 .
C1 H1 O26 1.00 2.42 2.886(2) 107.7 .
C1 H1 O36 1.00 2.44 2.900(2) 107.2 .
C12 H12 O32 0.95 2.41 2.970(2) 117.6 .

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.28
_refine_diff_density_rms         0.059