##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
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data_global
_audit_creation_method     SHELXL-97
_journal_data_validation_number     ?
_journal_date_recd_electronic     2008-04-18
_journal_date_accepted     2008-07-15
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      8
_journal_page_first     o1556
_journal_page_last     o1556
_journal_paper_category     QO
_journal_coeditor_code     GK2144
_publ_contact_author_name     'Professor B. T. Ibragimov'
_publ_contact_author_address
;
Institute of Bioorganic Chemistry
Academy of Sciences of Uzbekistan
H Abdullaev 83
Tashkent 100125
Uzbekistan
;
_publ_contact_author_email     bahtier@academy.uzsci.net
_publ_contact_author_fax     ' '
_publ_contact_author_phone     ' '
_publ_section_title
;
4'-Formylbenzo-15-crown-5
;
loop_
    _publ_author_name
    _publ_author_address
    'Fischer, Conrad'
;
Institut für Organische Chemie
TU Bergakademie Freiberg
Leipziger Strasse 29
D-09596 Freiberg/Sachsen
Germany
;
    'Helas, Stefanie F.'
;
Institut für Organische Chemie
TU Bergakademie Freiberg
Leipziger Strasse 29
D-09596 Freiberg/Sachsen
Germany
;
    'Seichter, Wilhelm'
;
Institut für Organische Chemie
TU Bergakademie Freiberg
Leipziger Strasse 29
D-09596 Freiberg/Sachsen
Germany
;
    'Weber, Edwin'
;
Institut für Organische Chemie
TU Bergakademie Freiberg
Leipziger Strasse 29
D-09596 Freiberg/Sachsen
Germany
;
    'Ibragimov, Bakhtiyar T.'
;
Institute of Bioorganic Chemistry
Academy of Sciences of Uzbekistan
H Abdullaev 83
Tashkent 100125
Uzbekistan
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
17-Formyl-2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-15,17,19-triene
;
_chemical_name_common     "4'-Formylbenzo-15-crown-5"
_chemical_formula_moiety     'C15 H20 O6'
_chemical_formula_sum     'C15 H20 O6'
_chemical_formula_iupac     'C15 H20 O6'
_chemical_formula_weight     296.31
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     18.0091(8)
_cell_length_b     9.6678(4)
_cell_length_c     8.1028(3)
_cell_angle_alpha     90.00
_cell_angle_beta     91.262(2)
_cell_angle_gamma     90.00
_cell_volume     1410.42(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9008
_cell_measurement_theta_min     2.39
_cell_measurement_theta_max     33.28
_cell_measurement_temperature     90(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.39
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.395
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     632
_exptl_absorpt_coefficient_mu     0.108
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min     0.8570
_exptl_absorpt_correction_T_max     0.9946
_exptl_special_details
;
;
_diffrn_ambient_temperature     90(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker Kappa APEXII CCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     18190
_diffrn_reflns_av_R_equivalents     0.0265
_diffrn_reflns_av_sigmaI/netI     0.0240
_diffrn_reflns_theta_min     3.09
_diffrn_reflns_theta_max     31.10
_diffrn_reflns_theta_full     31.10
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -26
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_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     4523
_reflns_number_gt     3716
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0478
_refine_ls_R_factor_gt     0.0368
_refine_ls_wR_factor_gt     0.1026
_refine_ls_wR_factor_ref     0.1155
_refine_ls_goodness_of_fit_ref     0.999
_refine_ls_restrained_S_all     0.999
_refine_ls_number_reflns     4523
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0681P)²+0.3911P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.281
_refine_diff_density_min     -0.219
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2004)'
_computing_cell_refinement     'SAINT (Bruker, 2004)'
_computing_data_reduction     'SAINT (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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 -0.03932(4) 0.76211(8) 0.74777(10) 0.02453(17) Uani d . 1 . .
    O O2 0.18803(4) 0.54926(7) 0.45384(9) 0.01606(14) Uani d . 1 . .
    O O3 0.25972(4) 0.29979(8) 0.55829(10) 0.02217(17) Uani d . 1 . .
    O O4 0.42078(4) 0.40116(8) 0.32578(9) 0.01872(15) Uani d . 1 . .
    O O5 0.41719(4) 0.72035(7) 0.34545(8) 0.01730(15) Uani d . 1 . .
    O O6 0.26420(4) 0.75557(7) 0.36194(9) 0.01609(14) Uani d . 1 . .
    C C1 0.15926(5) 0.67447(9) 0.49388(11) 0.01361(17) Uani d . 1 . .
    C C2 0.09428(5) 0.69566(10) 0.57629(11) 0.01540(17) Uani d . 1 . .
    H H2 0.0650 0.6190 0.6084 0.018 Uiso calc R 1 . .
    C C3 0.07132(5) 0.83094(10) 0.61289(11) 0.01618(18) Uani d . 1 . .
    C C4 0.11385(6) 0.94299(10) 0.56708(12) 0.01868(19) Uani d . 1 . .
    H H4 0.0984 1.0340 0.5940 0.022 Uiso calc R 1 . .
    C C5 0.17961(6) 0.92303(10) 0.48118(12) 0.01756(18) Uani d . 1 . .
    H H5 0.2085 1.0002 0.4487 0.021 Uiso calc R 1 . .
    C C6 0.20225(5) 0.78964(9) 0.44389(11) 0.01396(17) Uani d . 1 . .
    C C7 0.00239(5) 0.85268(11) 0.70205(12) 0.02018(19) Uani d . 1 . .
    H H7 -0.0109 0.9455 0.7262 0.024 Uiso calc R 1 . .
    C C8 0.14823(5) 0.43015(9) 0.50768(13) 0.01689(18) Uani d . 1 . .
    H H8A 0.0984 0.4269 0.4539 0.020 Uiso calc R 1 . .
    H H8B 0.1422 0.4329 0.6288 0.020 Uiso calc R 1 . .
    C C9 0.19286(5) 0.30593(10) 0.46010(14) 0.0203(2) Uani d . 1 . .
    H H9A 0.1633 0.2209 0.4769 0.024 Uiso calc R 1 . .
    H H9B 0.2052 0.3116 0.3418 0.024 Uiso calc R 1 . .
    C C10 0.32608(5) 0.28738(10) 0.46689(14) 0.0204(2) Uani d . 1 . .
    H H10A 0.3193 0.2140 0.3827 0.025 Uiso calc R 1 . .
    H H10B 0.3672 0.2589 0.5425 0.025 Uiso calc R 1 . .
    C C11 0.34702(5) 0.42146(10) 0.38202(12) 0.01686(18) Uani d . 1 . .
    H H11A 0.3126 0.4408 0.2879 0.020 Uiso calc R 1 . .
    H H11B 0.3453 0.4999 0.4604 0.020 Uiso calc R 1 . .
    C C12 0.44456(5) 0.49820(11) 0.20613(12) 0.01883(19) Uani d . 1 . .
    H H12A 0.4024 0.5185 0.1295 0.023 Uiso calc R 1 . .
    H H12B 0.4844 0.4554 0.1410 0.023 Uiso calc R 1 . .
    C C13 0.47328(5) 0.63335(11) 0.27812(12) 0.01947(19) Uani d . 1 . .
    H H13A 0.5106 0.6122 0.3662 0.023 Uiso calc R 1 . .
    H H13B 0.4988 0.6851 0.1905 0.023 Uiso calc R 1 . .
    C C14 0.37553(5) 0.79418(10) 0.22314(11) 0.01733(18) Uani d . 1 . .
    H H14A 0.3570 0.7297 0.1367 0.021 Uiso calc R 1 . .
    H H14B 0.4074 0.8642 0.1705 0.021 Uiso calc R 1 . .
    C C15 0.31127(5) 0.86389(10) 0.30465(11) 0.01632(18) Uani d . 1 . .
    H H15A 0.3291 0.9217 0.3982 0.020 Uiso calc R 1 . .
    H H15B 0.2840 0.9236 0.2247 0.020 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O1 0.0197(3) 0.0272(4) 0.0269(4) -0.0004(3) 0.0049(3) -0.0043(3)
    O2 0.0180(3) 0.0094(3) 0.0211(3) -0.0007(2) 0.0051(2) 0.0003(2)
    O3 0.0173(3) 0.0243(4) 0.0250(4) 0.0025(3) 0.0044(3) 0.0089(3)
    O4 0.0157(3) 0.0198(3) 0.0208(3) 0.0011(2) 0.0037(2) 0.0046(3)
    O5 0.0187(3) 0.0205(3) 0.0127(3) -0.0001(3) 0.0001(2) 0.0022(2)
    O6 0.0177(3) 0.0122(3) 0.0186(3) -0.0023(2) 0.0052(2) 0.0007(2)
    C1 0.0164(4) 0.0108(4) 0.0137(4) 0.0004(3) -0.0004(3) 0.0002(3)
    C2 0.0164(4) 0.0140(4) 0.0158(4) -0.0003(3) 0.0005(3) 0.0001(3)
    C3 0.0175(4) 0.0163(4) 0.0148(4) 0.0023(3) -0.0001(3) -0.0014(3)
    C4 0.0233(4) 0.0129(4) 0.0199(4) 0.0028(3) 0.0012(3) -0.0017(3)
    C5 0.0222(4) 0.0119(4) 0.0186(4) -0.0003(3) 0.0011(3) 0.0007(3)
    C6 0.0159(4) 0.0133(4) 0.0127(4) -0.0004(3) 0.0002(3) 0.0006(3)
    C7 0.0195(4) 0.0209(5) 0.0201(4) 0.0039(3) 0.0009(3) -0.0053(4)
    C8 0.0161(4) 0.0112(4) 0.0235(5) -0.0019(3) 0.0035(3) 0.0015(3)
    C9 0.0171(4) 0.0124(4) 0.0314(5) -0.0006(3) 0.0021(4) -0.0001(4)
    C10 0.0169(4) 0.0171(4) 0.0274(5) 0.0023(3) 0.0044(3) 0.0054(4)
    C11 0.0162(4) 0.0154(4) 0.0191(4) -0.0003(3) 0.0033(3) -0.0001(3)
    C12 0.0193(4) 0.0218(5) 0.0156(4) 0.0005(3) 0.0043(3) 0.0017(3)
    C13 0.0156(4) 0.0230(5) 0.0199(4) -0.0019(3) 0.0023(3) 0.0025(4)
    C14 0.0185(4) 0.0208(4) 0.0127(4) -0.0019(3) 0.0009(3) 0.0043(3)
    C15 0.0194(4) 0.0141(4) 0.0156(4) -0.0040(3) 0.0008(3) 0.0027(3)
_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 C7 . 1.2168(13) ?
    O2 C1 . 1.3589(11) ?
    O2 C8 . 1.4296(11) ?
    O3 C10 . 1.4249(12) ?
    O3 C9 . 1.4297(13) ?
    O4 C12 . 1.4219(12) ?
    O4 C11 . 1.4275(11) ?
    O5 C14 . 1.4219(12) ?
    O5 C13 . 1.4318(12) ?
    O6 C6 . 1.3516(11) ?
    O6 C15 . 1.4311(11) ?
    C1 C2 . 1.3755(12) ?
    C1 C6 . 1.4202(12) ?
    C2 C3 . 1.4052(13) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.3822(13) ?
    C3 C7 . 1.4651(13) ?
    C4 C5 . 1.4003(13) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.3877(13) ?
    C5 H5 . 0.9500 ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.5001(13) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 C11 . 1.5189(13) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C12 C13 . 1.5171(15) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 C15 . 1.5044(13) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
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
    C1 O2 C8 . . 116.64(7) ?
    C10 O3 C9 . . 114.84(8) ?
    C12 O4 C11 . . 115.04(7) ?
    C14 O5 C13 . . 113.27(7) ?
    C6 O6 C15 . . 118.83(7) ?
    O2 C1 C2 . . 125.56(8) ?
    O2 C1 C6 . . 114.66(8) ?
    C2 C1 C6 . . 119.78(8) ?
    C1 C2 C3 . . 119.90(9) ?
    C1 C2 H2 . . 120.0 ?
    C3 C2 H2 . . 120.0 ?
    C4 C3 C2 . . 120.36(9) ?
    C4 C3 C7 . . 120.03(9) ?
    C2 C3 C7 . . 119.61(9) ?
    C3 C4 C5 . . 120.35(9) ?
    C3 C4 H4 . . 119.8 ?
    C5 C4 H4 . . 119.8 ?
    C6 C5 C4 . . 119.47(9) ?
    C6 C5 H5 . . 120.3 ?
    C4 C5 H5 . . 120.3 ?
    O6 C6 C5 . . 125.67(8) ?
    O6 C6 C1 . . 114.21(8) ?
    C5 C6 C1 . . 120.12(8) ?
    O1 C7 C3 . . 125.61(10) ?
    O1 C7 H7 . . 117.2 ?
    C3 C7 H7 . . 117.2 ?
    O2 C8 C9 . . 106.94(7) ?
    O2 C8 H8A . . 110.3 ?
    C9 C8 H8A . . 110.3 ?
    O2 C8 H8B . . 110.3 ?
    C9 C8 H8B . . 110.3 ?
    H8A C8 H8B . . 108.6 ?
    O3 C9 C8 . . 109.85(8) ?
    O3 C9 H9A . . 109.7 ?
    C8 C9 H9A . . 109.7 ?
    O3 C9 H9B . . 109.7 ?
    C8 C9 H9B . . 109.7 ?
    H9A C9 H9B . . 108.2 ?
    O3 C10 C11 . . 112.51(8) ?
    O3 C10 H10A . . 109.1 ?
    C11 C10 H10A . . 109.1 ?
    O3 C10 H10B . . 109.1 ?
    C11 C10 H10B . . 109.1 ?
    H10A C10 H10B . . 107.8 ?
    O4 C11 C10 . . 105.62(7) ?
    O4 C11 H11A . . 110.6 ?
    C10 C11 H11A . . 110.6 ?
    O4 C11 H11B . . 110.6 ?
    C10 C11 H11B . . 110.6 ?
    H11A C11 H11B . . 108.7 ?
    O4 C12 C13 . . 114.29(8) ?
    O4 C12 H12A . . 108.7 ?
    C13 C12 H12A . . 108.7 ?
    O4 C12 H12B . . 108.7 ?
    C13 C12 H12B . . 108.7 ?
    H12A C12 H12B . . 107.6 ?
    O5 C13 C12 . . 114.52(8) ?
    O5 C13 H13A . . 108.6 ?
    C12 C13 H13A . . 108.6 ?
    O5 C13 H13B . . 108.6 ?
    C12 C13 H13B . . 108.6 ?
    H13A C13 H13B . . 107.6 ?
    O5 C14 C15 . . 108.54(7) ?
    O5 C14 H14A . . 110.0 ?
    C15 C14 H14A . . 110.0 ?
    O5 C14 H14B . . 110.0 ?
    C15 C14 H14B . . 110.0 ?
    H14A C14 H14B . . 108.4 ?
    O6 C15 C14 . . 106.35(7) ?
    O6 C15 H15A . . 110.5 ?
    C14 C15 H15A . . 110.5 ?
    O6 C15 H15B . . 110.5 ?
    C14 C15 H15B . . 110.5 ?
    H15A C15 H15B . . 108.7 ?
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
    C8 O2 C1 C2 . . . . -2.33(13) ?
    C8 O2 C1 C6 . . . . 177.50(8) ?
    O2 C1 C2 C3 . . . . 178.83(9) ?
    C6 C1 C2 C3 . . . . -0.99(14) ?
    C1 C2 C3 C4 . . . . -0.25(14) ?
    C1 C2 C3 C7 . . . . -179.43(9) ?
    C2 C3 C4 C5 . . . . 1.12(15) ?
    C7 C3 C4 C5 . . . . -179.71(9) ?
    C3 C4 C5 C6 . . . . -0.71(15) ?
    C15 O6 C6 C5 . . . . -1.01(14) ?
    C15 O6 C6 C1 . . . . 179.48(8) ?
    C4 C5 C6 O6 . . . . 179.97(9) ?
    C4 C5 C6 C1 . . . . -0.54(14) ?
    O2 C1 C6 O6 . . . . 1.10(12) ?
    C2 C1 C6 O6 . . . . -179.06(8) ?
    O2 C1 C6 C5 . . . . -178.45(8) ?
    C2 C1 C6 C5 . . . . 1.40(14) ?
    C4 C3 C7 O1 . . . . 179.75(10) ?
    C2 C3 C7 O1 . . . . -1.06(16) ?
    C1 O2 C8 C9 . . . . -176.14(8) ?
    C10 O3 C9 C8 . . . . -127.42(9) ?
    O2 C8 C9 O3 . . . . 69.34(10) ?
    C9 O3 C10 C11 . . . . 73.81(11) ?
    C12 O4 C11 C10 . . . . 164.16(8) ?
    O3 C10 C11 O4 . . . . 168.42(8) ?
    C11 O4 C12 C13 . . . . 82.80(10) ?
    C14 O5 C13 C12 . . . . -78.28(10) ?
    O4 C12 C13 O5 . . . . -71.10(11) ?
    C13 O5 C14 C15 . . . . 171.27(8) ?
    C6 O6 C15 C14 . . . . 178.69(8) ?
    O5 C14 C15 O6 . . . . -65.61(9) ?
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
    _geom_hbond_publ_flag
    C13 H13B O4 2_655 0.99 2.55 3.3351(10) 137 y
    C14 H14A O5 4_575 0.99 2.66 3.1700(12) 112 y
    C8 H8A O1 3_566 0.99 2.66 3.3775(13) 130 y
