##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2011-02-16
_journal_date_accepted     2011-03-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      4
_journal_page_first     o826
_journal_page_last     o826
_journal_paper_category     QO
_journal_coeditor_code     EZ2236
_publ_contact_author_name     ' Edward RT Tiekink '
_publ_contact_author_address
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_contact_author_email
;
edward.tiekink@gmail.com
;
_publ_contact_author_fax     ' +60 3 7967 4193 '
_publ_contact_author_phone     ' +60 3 7967 6775 '
_publ_section_title
;
4-Formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Rusnah Syahila Duali Hussen' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Thorsten Heidelberg'
;
Additional correspondence author, e-mail: heidelberg@um.edu.my.
;
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Nasrul Zamani Mohd Rodzi' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Ng, Seik Weng' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Tiekink, Edward R. T.' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-Formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H24 O11'
_chemical_formula_sum     'C21 H24 O11'
_chemical_formula_iupac     'C21 H24 O11'
_chemical_formula_weight     452.40
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     11.8358(4)
_cell_length_b     5.6664(2)
_cell_length_c     17.5079(6)
_cell_angle_alpha     90
_cell_angle_beta     109.616(4)
_cell_angle_gamma     90
_cell_volume     1106.05(7)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5487
_cell_measurement_theta_min     2.5
_cell_measurement_theta_max     29.3
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.358
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     476
_exptl_absorpt_coefficient_mu     0.111
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Agilent, 2010)'
_exptl_absorpt_correction_T_min     0.596
_exptl_absorpt_correction_T_max     1.000
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator     Mirror
_diffrn_measurement_device_type
;
Agilent Supernova Dual diffractometer with an Atlas detector
;
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.4041
_diffrn_reflns_number     10396
_diffrn_reflns_av_R_equivalents     0.051
_diffrn_reflns_av_sigmaI/netI     0.037
_diffrn_reflns_theta_min     2.5
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_theta_full     27.5
_diffrn_measured_fraction_theta_max     0.988
_diffrn_measured_fraction_theta_full     0.988
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2768
_reflns_number_gt     2535
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.040
_refine_ls_R_factor_gt     0.035
_refine_ls_wR_factor_gt     0.083
_refine_ls_wR_factor_ref     0.086
_refine_ls_goodness_of_fit_ref     1.05
_refine_ls_restrained_S_all     1.05
_refine_ls_number_reflns     2768
_refine_ls_number_parameters     293
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0424P)²+0.1621P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.21
_refine_diff_density_min     -0.21
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
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 0.0000
                         '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 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis PRO (Agilent, 2010)'
_computing_cell_refinement     'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction     'CrysAlis PRO (Agilent, 2010)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                      'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material     'publCIF (Westrip, 2010)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.52081(12) 0.4982(3) 0.29215(8) 0.0188(3) Uani d . 1 . .
    O O2 0.48738(13) 0.0896(3) 0.37091(9) 0.0240(4) Uani d . 1 . .
    O O3 0.55891(13) -0.1643(3) 0.47497(9) 0.0243(4) Uani d . 1 . .
    O O4 0.75837(12) 0.6298(3) 0.39447(8) 0.0184(3) Uani d . 1 . .
    O O5 0.86847(14) 0.3841(3) 0.49186(9) 0.0283(4) Uani d . 1 . .
    O O6 0.83224(12) 0.7065(3) 0.26663(8) 0.0202(3) Uani d . 1 . .
    O O7 0.95682(14) 0.3988(3) 0.27801(9) 0.0271(4) Uani d . 1 . .
    O O8 0.61785(14) 0.7131(3) 0.12877(9) 0.0202(3) Uani d . 1 . .
    O O9 0.61716(16) 1.1080(3) 0.13951(10) 0.0304(4) Uani d . 1 . .
    O O10 0.41232(13) 0.7100(3) 0.18039(8) 0.0213(3) Uani d . 1 . .
    O O11 -0.15194(15) 0.5245(5) 0.06218(12) 0.0490(6) Uani d . 1 . .
    C C1 0.61385(17) 0.3269(4) 0.32349(12) 0.0180(4) Uani d . 1 . .
    H H1 0.6016 0.1990 0.2821 0.022 Uiso calc R 1 . .
    C C2 0.73547(18) 0.4392(4) 0.33610(12) 0.0178(4) Uani d . 1 . .
    H H2 0.8001 0.3174 0.3549 0.021 Uiso calc R 1 . .
    C C3 0.73421(17) 0.5437(4) 0.25518(12) 0.0177(4) Uani d . 1 . .
    H H3 0.7421 0.4124 0.2191 0.021 Uiso calc R 1 . .
    C C4 0.62145(17) 0.6840(4) 0.21135(11) 0.0177(4) Uani d . 1 . .
    H H4 0.6253 0.8420 0.2376 0.021 Uiso calc R 1 . .
    C C5 0.50894(18) 0.5541(4) 0.21107(12) 0.0182(4) Uani d . 1 . .
    H H5 0.4966 0.4081 0.1772 0.022 Uiso calc R 1 . .
    C C6 0.59907(18) 0.2203(4) 0.39814(12) 0.0216(5) Uani d . 1 . .
    H H6A 0.6670 0.1138 0.4253 0.026 Uiso calc R 1 . .
    H H6B 0.5958 0.3454 0.4368 0.026 Uiso calc R 1 . .
    C C7 0.47923(18) -0.0968(4) 0.41586(12) 0.0205(4) Uani d . 1 . .
    C C8 0.35738(19) -0.2058(5) 0.38251(13) 0.0272(5) Uani d . 1 . .
    H H8A 0.3622 -0.3731 0.3974 0.041 Uiso calc R 1 . .
    H H8B 0.3277 -0.1909 0.3233 0.041 Uiso calc R 1 . .
    H H8C 0.3024 -0.1247 0.4049 0.041 Uiso calc R 1 . .
    C C9 0.83088(18) 0.5785(4) 0.47134(12) 0.0195(4) Uani d . 1 . .
    C C10 0.8534(2) 0.7915(4) 0.52407(13) 0.0246(5) Uani d . 1 . .
    H H10A 0.9152 0.7559 0.5762 0.037 Uiso calc R 1 . .
    H H10B 0.7791 0.8375 0.5332 0.037 Uiso calc R 1 . .
    H H10C 0.8807 0.9212 0.4976 0.037 Uiso calc R 1 . .
    C C11 0.94103(19) 0.6087(5) 0.27887(12) 0.0221(5) Uani d . 1 . .
    C C12 1.0356(2) 0.7935(5) 0.29539(14) 0.0301(6) Uani d . 1 . .
    H H12A 1.0988 0.7413 0.2746 0.045 Uiso calc R 1 . .
    H H12B 1.0701 0.8202 0.3540 0.045 Uiso calc R 1 . .
    H H12C 1.0003 0.9407 0.2684 0.045 Uiso calc R 1 . .
    C C13 0.61949(19) 0.9346(4) 0.10083(13) 0.0208(5) Uani d . 1 . .
    C C14 0.6223(2) 0.9316(5) 0.01601(13) 0.0284(5) Uani d . 1 . .
    H H14A 0.6497 1.0852 0.0034 0.043 Uiso calc R 1 . .
    H H14B 0.5416 0.8993 -0.0219 0.043 Uiso calc R 1 . .
    H H14C 0.6774 0.8081 0.0111 0.043 Uiso calc R 1 . .
    C C15 0.29775(18) 0.6182(5) 0.16131(12) 0.0214(5) Uani d . 1 . .
    C C16 0.2083(2) 0.7649(5) 0.11247(13) 0.0269(5) Uani d . 1 . .
    H H16 0.2281 0.9110 0.0935 0.032 Uiso calc R 1 . .
    C C17 0.0891(2) 0.6936(5) 0.09193(14) 0.0310(6) Uani d . 1 . .
    H H17 0.0271 0.7924 0.0588 0.037 Uiso calc R 1 . .
    C C18 0.0601(2) 0.4804(5) 0.11914(13) 0.0282(5) Uani d . 1 . .
    C C19 0.1514(2) 0.3361(5) 0.16730(13) 0.0275(5) Uani d . 1 . .
    H H19 0.1317 0.1889 0.1856 0.033 Uiso calc R 1 . .
    C C20 0.27087(19) 0.4037(4) 0.18905(13) 0.0246(5) Uani d . 1 . .
    H H20 0.3328 0.3050 0.2222 0.030 Uiso calc R 1 . .
    C C21 -0.0667(2) 0.4052(6) 0.09904(14) 0.0369(6) Uani d . 1 . .
    H H21 -0.0816 0.2530 0.1163 0.044 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C5 . 1.415(2) ?
    O1 C1 . 1.432(2) ?
    O2 C7 . 1.340(3) ?
    O2 C6 . 1.449(3) ?
    O3 C7 . 1.205(3) ?
    O4 C9 . 1.362(2) ?
    O4 C2 . 1.448(2) ?
    O5 C9 . 1.197(3) ?
    O6 C11 . 1.351(3) ?
    O6 C3 . 1.443(2) ?
    O7 C11 . 1.205(3) ?
    O8 C13 . 1.350(3) ?
    O8 C4 . 1.441(2) ?
    O9 C13 . 1.199(3) ?
    O10 C15 . 1.384(3) ?
    O10 C5 . 1.401(2) ?
    O11 C21 . 1.206(3) ?
    C1 C6 . 1.502(3) ?
    C1 C2 . 1.521(3) ?
    C1 H1 . 1.0000 ?
    C2 C3 . 1.531(3) ?
    C2 H2 . 1.0000 ?
    C3 C4 . 1.521(3) ?
    C3 H3 . 1.0000 ?
    C4 C5 . 1.520(3) ?
    C4 H4 . 1.0000 ?
    C5 H5 . 1.0000 ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C7 C8 . 1.496(3) ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
    C9 C10 . 1.488(3) ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C11 C12 . 1.489(3) ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 0.9800 ?
    C13 C14 . 1.497(3) ?
    C14 H14A . 0.9800 ?
    C14 H14B . 0.9800 ?
    C14 H14C . 0.9800 ?
    C15 C20 . 1.385(3) ?
    C15 C16 . 1.391(3) ?
    C16 C17 . 1.393(3) ?
    C16 H16 . 0.9500 ?
    C17 C18 . 1.384(4) ?
    C17 H17 . 0.9500 ?
    C18 C19 . 1.391(3) ?
    C18 C21 . 1.484(3) ?
    C19 C20 . 1.389(3) ?
    C19 H19 . 0.9500 ?
    C20 H20 . 0.9500 ?
    C21 H21 . 0.9500 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C5 O1 C1 . . 109.93(14) ?
    C7 O2 C6 . . 116.57(16) ?
    C9 O4 C2 . . 116.39(17) ?
    C11 O6 C3 . . 116.03(17) ?
    C13 O8 C4 . . 118.07(17) ?
    C15 O10 C5 . . 117.57(17) ?
    O1 C1 C6 . . 107.86(16) ?
    O1 C1 C2 . . 109.91(17) ?
    C6 C1 C2 . . 115.02(17) ?
    O1 C1 H1 . . 107.9 ?
    C6 C1 H1 . . 107.9 ?
    C2 C1 H1 . . 107.9 ?
    O4 C2 C1 . . 111.00(16) ?
    O4 C2 C3 . . 107.82(17) ?
    C1 C2 C3 . . 108.23(16) ?
    O4 C2 H2 . . 109.9 ?
    C1 C2 H2 . . 109.9 ?
    C3 C2 H2 . . 109.9 ?
    O6 C3 C4 . . 105.32(16) ?
    O6 C3 C2 . . 111.18(16) ?
    C4 C3 C2 . . 113.79(16) ?
    O6 C3 H3 . . 108.8 ?
    C4 C3 H3 . . 108.8 ?
    C2 C3 H3 . . 108.8 ?
    O8 C4 C5 . . 108.73(16) ?
    O8 C4 C3 . . 106.93(15) ?
    C5 C4 C3 . . 111.57(17) ?
    O8 C4 H4 . . 109.9 ?
    C5 C4 H4 . . 109.9 ?
    C3 C4 H4 . . 109.9 ?
    O10 C5 O1 . . 108.61(15) ?
    O10 C5 C4 . . 107.29(17) ?
    O1 C5 C4 . . 108.26(16) ?
    O10 C5 H5 . . 110.9 ?
    O1 C5 H5 . . 110.9 ?
    C4 C5 H5 . . 110.9 ?
    O2 C6 C1 . . 106.20(16) ?
    O2 C6 H6A . . 110.5 ?
    C1 C6 H6A . . 110.5 ?
    O2 C6 H6B . . 110.5 ?
    C1 C6 H6B . . 110.5 ?
    H6A C6 H6B . . 108.7 ?
    O3 C7 O2 . . 124.39(19) ?
    O3 C7 C8 . . 125.4(2) ?
    O2 C7 C8 . . 110.25(18) ?
    C7 C8 H8A . . 109.5 ?
    C7 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C7 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    O5 C9 O4 . . 122.7(2) ?
    O5 C9 C10 . . 126.07(19) ?
    O4 C9 C10 . . 111.22(19) ?
    C9 C10 H10A . . 109.5 ?
    C9 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C9 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    O7 C11 O6 . . 123.1(2) ?
    O7 C11 C12 . . 125.9(2) ?
    O6 C11 C12 . . 110.9(2) ?
    C11 C12 H12A . . 109.5 ?
    C11 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C11 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    O9 C13 O8 . . 123.49(19) ?
    O9 C13 C14 . . 125.6(2) ?
    O8 C13 C14 . . 110.91(19) ?
    C13 C14 H14A . . 109.5 ?
    C13 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C13 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    O10 C15 C20 . . 124.53(19) ?
    O10 C15 C16 . . 113.9(2) ?
    C20 C15 C16 . . 121.5(2) ?
    C15 C16 C17 . . 118.7(2) ?
    C15 C16 H16 . . 120.6 ?
    C17 C16 H16 . . 120.6 ?
    C18 C17 C16 . . 120.8(2) ?
    C18 C17 H17 . . 119.6 ?
    C16 C17 H17 . . 119.6 ?
    C17 C18 C19 . . 119.3(2) ?
    C17 C18 C21 . . 121.1(2) ?
    C19 C18 C21 . . 119.5(3) ?
    C20 C19 C18 . . 121.1(2) ?
    C20 C19 H19 . . 119.5 ?
    C18 C19 H19 . . 119.5 ?
    C15 C20 C19 . . 118.6(2) ?
    C15 C20 H20 . . 120.7 ?
    C19 C20 H20 . . 120.7 ?
    O11 C21 C18 . . 124.3(3) ?
    O11 C21 H21 . . 117.8 ?
    C18 C21 H21 . . 117.8 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C5 O1 C1 C6 . . . . -163.31(17) ?
    C5 O1 C1 C2 . . . . 70.6(2) ?
    C9 O4 C2 C1 . . . . 100.1(2) ?
    C9 O4 C2 C3 . . . . -141.53(17) ?
    O1 C1 C2 O4 . . . . 61.5(2) ?
    C6 C1 C2 O4 . . . . -60.5(2) ?
    O1 C1 C2 C3 . . . . -56.7(2) ?
    C6 C1 C2 C3 . . . . -178.60(18) ?
    C11 O6 C3 C4 . . . . -158.49(16) ?
    C11 O6 C3 C2 . . . . 77.8(2) ?
    O4 C2 C3 O6 . . . . 44.2(2) ?
    C1 C2 C3 O6 . . . . 164.33(16) ?
    O4 C2 C3 C4 . . . . -74.5(2) ?
    C1 C2 C3 C4 . . . . 45.6(2) ?
    C13 O8 C4 C5 . . . . 120.0(2) ?
    C13 O8 C4 C3 . . . . -119.44(19) ?
    O6 C3 C4 O8 . . . . 73.70(19) ?
    C2 C3 C4 O8 . . . . -164.29(17) ?
    O6 C3 C4 C5 . . . . -167.54(16) ?
    C2 C3 C4 C5 . . . . -45.5(2) ?
    C15 O10 C5 O1 . . . . -74.1(2) ?
    C15 O10 C5 C4 . . . . 169.11(16) ?
    C1 O1 C5 O10 . . . . 176.18(16) ?
    C1 O1 C5 C4 . . . . -67.6(2) ?
    O8 C4 C5 O10 . . . . -70.80(19) ?
    C3 C4 C5 O10 . . . . 171.51(15) ?
    O8 C4 C5 O1 . . . . 172.16(16) ?
    C3 C4 C5 O1 . . . . 54.5(2) ?
    C7 O2 C6 C1 . . . . 151.59(18) ?
    O1 C1 C6 O2 . . . . 66.5(2) ?
    C2 C1 C6 O2 . . . . -170.44(17) ?
    C6 O2 C7 O3 . . . . -2.2(3) ?
    C6 O2 C7 C8 . . . . 177.27(18) ?
    C2 O4 C9 O5 . . . . -4.5(3) ?
    C2 O4 C9 C10 . . . . 176.56(17) ?
    C3 O6 C11 O7 . . . . 2.3(3) ?
    C3 O6 C11 C12 . . . . -176.14(16) ?
    C4 O8 C13 O9 . . . . -4.2(3) ?
    C4 O8 C13 C14 . . . . 176.78(17) ?
    C5 O10 C15 C20 . . . . 17.7(3) ?
    C5 O10 C15 C16 . . . . -164.09(18) ?
    O10 C15 C16 C17 . . . . -177.76(19) ?
    C20 C15 C16 C17 . . . . 0.5(3) ?
    C15 C16 C17 C18 . . . . -0.3(3) ?
    C16 C17 C18 C19 . . . . -0.2(3) ?
    C16 C17 C18 C21 . . . . 178.7(2) ?
    C17 C18 C19 C20 . . . . 0.6(3) ?
    C21 C18 C19 C20 . . . . -178.3(2) ?
    O10 C15 C20 C19 . . . . 177.9(2) ?
    C16 C15 C20 C19 . . . . -0.2(3) ?
    C18 C19 C20 C15 . . . . -0.4(3) ?
    C17 C18 C21 O11 . . . . -3.8(4) ?
    C19 C18 C21 O11 . . . . 175.1(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    C3 H3 O9 1_545 1.00 2.39 3.199(3) 137
    C5 H5 O9 1_545 1.00 2.45 3.268(3) 139
    C10 H10b O3 1_565 0.98 2.46 3.307(3) 145
    C12 H12b O5 2_756 0.98 2.57 3.548(3) 172
    C14 H14c O11 1_655 0.98 2.50 3.415(4) 155
