##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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     2006-10-06
_journal_date_accepted     2006-11-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      1
_journal_page_first     m392
_journal_page_last     m393
_journal_paper_category     EO
_journal_coeditor_code     KP2056
_publ_contact_author_name     'Zun-Le Xu'
_publ_contact_author_address
; School of Chemistry and Chemical Engineering
  University of Sun Yat-Sen
  Guangzhou\ 510275
    China
;
_publ_contact_author_email     wxzqq1234@163.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     '00862013316227980'
_publ_section_title
;
Methyl 2,2',7'-trihydroxy-1,1'-binaphthalene-3-carboxylate acetone solvate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Xiu-Zhen Wang' .
;
College of Pharmacy GuangDong Pharmaceutical University
Guangzhou 510224
People's Republic of China
;
    'Zhao-Xuen Lian' .
;
School of Chemistry and Chemical Engineering
University of Sun Yat-Sen
Guangzhou 510275
People's Republic of China
;
    'Zun-Le Xu' .
;
School of Chemistry and Chemical Engineering
University of Sun Yat-Sen
Guangzhou 510275
People's Republic of China
;
data_I
_chemical_name_systematic
;
Methyl 2,2',7'-trihydroxy-1,1'-binaphthalene-3-carboxylate acetone solvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H16 O5, C3 H6 O'
_chemical_formula_sum     'C25 H22 O6'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C22 H16 O5, C3 H6 O'
_chemical_formula_weight     418.43
_chemical_melting_point     454
_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     13.477(4)
_cell_length_b     12.062(4)
_cell_length_c     14.049(4)
_cell_angle_alpha     90.00
_cell_angle_beta     109.223(6)
_cell_angle_gamma     90.00
_cell_volume     2156.5(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     12
_cell_measurement_theta_max     18
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.289
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     880
_exptl_absorpt_coefficient_mu     0.092
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9572
_exptl_absorpt_correction_T_max     0.9711
_exptl_special_details
;
 IR (KBr,
\ncm⁻¹) 3314 (Ar---OH), 3172, 2947, 2910, 1831 (CO), 1690, 1514, 1320, 1216,
825; ¹H NMR (DMSO): δ 10.26 (s, 1H), 9.18 (s, 1H), 9.14
(s, 1H), 8.67 (s, 1H), 8.07--8.04 (m, 1H), 7.70
(d, J = 8.7 Hz, 1H), 7.66 (d, J = 8.7 Hz, 1H),
7.38--7.33 (m, 2H), 7.05 (d, J = 8.7 Hz, 1H), 7.01--6.98
(m, 1H), 6.76 (dd, J = 8.7, 2.1 Hz, 1H), 6.16 (s,
1H), 4.01 (s, 3H); ¹³C NMR (DMSO): δ 170.5, 156.3, 153.9, 137.5,
136.9, 136.2, 132.4, 130.4, 130.3, 129.8, 129.6, 127.6, 125.2, 124.5, 123.5,
119.3, 115.6, 115.1, 113.2, 107.9, 106.3, 53.8; FAB-MS, m*/z*
(%): 360 ([M]⁺, 16). Analysis calculated for C₂₂H₁₆O₅: C 73.33,
H 4.48%; found: C 72.63, H 4.54.
;
_diffrn_ambient_temperature     293(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 SMART CCD area-detector'
_diffrn_measurement_method     'φ and\ w'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11034
_diffrn_reflns_av_R_equivalents     0.0211
_diffrn_reflns_av_sigmaI/netI     0.0266
_diffrn_reflns_theta_min     1.60
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.986
_diffrn_measured_fraction_theta_full     0.986
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -17
_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 > 2sigma(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     4184
_reflns_number_gt     2707
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0713
_refine_ls_R_factor_gt     0.0402
_refine_ls_wR_factor_gt     0.1006
_refine_ls_wR_factor_ref     0.1192
_refine_ls_goodness_of_fit_ref     1.020
_refine_ls_restrained_S_all     1.020
_refine_ls_number_reflns     4184
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0542P)²+0.4103P] 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     0.154
_refine_diff_density_min     -0.156
_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     'SMART (Bruker, 1997)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1997)'
_computing_publication_material     'SHELXTL'
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
    C C1 0.38132(17) 0.00879(16) 0.69682(14) 0.0597(5) Uani d . 1 . .
    C C2 0.40538(13) 0.06862(14) 0.61593(12) 0.0460(4) Uani d . 1 . .
    C C3 0.50706(13) 0.08238(14) 0.61746(12) 0.0470(4) Uani d . 1 . .
    H H3 0.5615 0.0515 0.6699 0.056 Uiso calc R 1 . .
    C C4 0.53069(12) 0.14155(13) 0.54227(12) 0.0435(4) Uani d . 1 . .
    C C5 0.63551(14) 0.15730(17) 0.54455(15) 0.0588(5) Uani d . 1 . .
    H H5 0.6901 0.1242 0.5954 0.071 Uiso calc R 1 . .
    C C6 0.65771(16) 0.2195(2) 0.47434(18) 0.0742(6) Uani d . 1 . .
    H H6 0.7271 0.2305 0.4777 0.089 Uiso calc R 1 . .
    C C7 0.57552(17) 0.2673(2) 0.39644(18) 0.0758(6) Uani d . 1 . .
    H H7 0.5912 0.3107 0.3486 0.091 Uiso calc R 1 . .
    C C8 0.47325(15) 0.25172(17) 0.38902(15) 0.0590(5) Uani d . 1 . .
    H H8 0.4202 0.2832 0.3356 0.071 Uiso calc R 1 . .
    C C9 0.44692(13) 0.18821(13) 0.46158(12) 0.0427(4) Uani d . 1 . .
    C C10 0.34112(12) 0.17120(13) 0.45767(12) 0.0415(4) Uani d . 1 . .
    C C11 0.32211(13) 0.11197(14) 0.53332(13) 0.0462(4) Uani d . 1 . .
    C C12 0.25168(12) 0.21688(14) 0.37270(12) 0.0426(4) Uani d . 1 . .
    C C13 0.22059(13) 0.16622(15) 0.28017(13) 0.0480(4) Uani d . 1 . .
    C C14 0.13745(14) 0.20868(16) 0.19849(13) 0.0524(5) Uani d . 1 . .
    H H14 0.1192 0.1743 0.1358 0.063 Uiso calc R 1 . .
    C C15 0.08415(14) 0.29957(15) 0.21130(13) 0.0527(5) Uani d . 1 . .
    H H15 0.0285 0.3260 0.1573 0.063 Uiso calc R 1 . .
    C C16 0.11121(13) 0.35473(14) 0.30436(12) 0.0456(4) Uani d . 1 . .
    C C17 0.05759(14) 0.44955(16) 0.31990(14) 0.0548(5) Uani d . 1 . .
    H H17 0.0002 0.4754 0.2674 0.066 Uiso calc R 1 . .
    C C18 0.08707(15) 0.50417(16) 0.40895(14) 0.0575(5) Uani d . 1 . .
    H H18 0.0502 0.5666 0.4173 0.069 Uiso calc R 1 . .
    C C19 0.17365(14) 0.46595(14) 0.48867(13) 0.0486(4) Uani d . 1 . .
    C C20 0.22664(13) 0.37280(14) 0.47824(12) 0.0455(4) Uani d . 1 . .
    H H20 0.2827 0.3476 0.5325 0.055 Uiso calc R 1 . .
    C C21 0.19743(12) 0.31431(13) 0.38620(12) 0.0421(4) Uani d . 1 . .
    C C22 0.4490(2) -0.0765(3) 0.85632(19) 0.1184(11) Uani d . 1 . .
    H H22A 0.3945 -0.0400 0.8745 0.178 Uiso calc R 1 . .
    H H22B 0.5128 -0.0763 0.9129 0.178 Uiso calc R 1 . .
    H H22C 0.4285 -0.1516 0.8370 0.178 Uiso calc R 1 . .
    O O1 0.29313(13) -0.01235(15) 0.69627(12) 0.0893(5) Uani d . 1 . .
    O O2 0.46592(12) -0.01871(12) 0.77295(10) 0.0758(4) Uani d . 1 . .
    O O3 0.22035(9) 0.09608(13) 0.52700(11) 0.0728(4) Uani d . 1 . .
    H H3A 0.2182 0.0612 0.5764 0.109 Uiso calc R 1 . .
    O O4 0.27330(11) 0.07307(11) 0.26864(9) 0.0671(4) Uani d . 1 . .
    H H4 0.2492 0.0512 0.2103 0.101 Uiso calc R 1 . .
    O O5 0.20537(11) 0.52020(11) 0.57979(9) 0.0635(4) Uani d . 1 . .
    H H5A 0.1715 0.5776 0.5751 0.095 Uiso calc R 1 . .
    C C23 0.16069(19) 0.7582(2) 0.72903(18) 0.0896(7) Uani d . 1 . .
    H H23C 0.1895 0.6847 0.7368 0.134 Uiso calc R 1 . .
    H H23B 0.1176 0.7668 0.7710 0.134 Uiso calc R 1 . .
    H H23A 0.2168 0.8113 0.7485 0.134 Uiso calc R 1 . .
    C C24 0.09660(15) 0.77646(17) 0.62297(16) 0.0573(5) Uani d . 1 . .
    C C25 0.03031(18) 0.8766(2) 0.59792(18) 0.0865(7) Uani d . 1 . .
    H H25C 0.0025 0.8850 0.5260 0.130 Uiso calc R 1 . .
    H H25B 0.0718 0.9405 0.6269 0.130 Uiso calc R 1 . .
    H H25A -0.0265 0.8697 0.6245 0.130 Uiso calc R 1 . .
    O O6 0.09691(13) 0.71208(12) 0.55727(12) 0.0806(5) Uani d . 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 O1 . 1.213(2) ?
    C1 O2 . 1.323(2) ?
    C1 C2 . 1.470(3) ?
    C2 C3 . 1.373(2) ?
    C2 C11 . 1.422(2) ?
    C3 C4 . 1.396(2) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.415(2) ?
    C4 C9 . 1.426(2) ?
    C5 C6 . 1.349(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.399(3) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.361(3) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.411(2) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.424(2) ?
    C10 C11 . 1.373(2) ?
    C10 C12 . 1.495(2) ?
    C11 O3 . 1.358(2) ?
    C12 C13 . 1.371(2) ?
    C12 C21 . 1.429(2) ?
    C13 O4 . 1.367(2) ?
    C13 C14 . 1.410(2) ?
    C14 C15 . 1.355(2) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.404(2) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.408(2) ?
    C16 C21 . 1.425(2) ?
    C17 C18 . 1.353(3) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.403(3) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.365(2) ?
    C19 O5 . 1.375(2) ?
    C20 C21 . 1.411(2) ?
    C20 H20 . 0.9300 ?
    C22 O2 . 1.444(3) ?
    C22 H22A . 0.9600 ?
    C22 H22B . 0.9600 ?
    C22 H22C . 0.9600 ?
    O3 H3A . 0.8200 ?
    O4 H4 . 0.8200 ?
    O5 H5A . 0.8200 ?
    C23 C24 . 1.472(3) ?
    C23 H23C . 0.9600 ?
    C23 H23B . 0.9600 ?
    C23 H23A . 0.9600 ?
    C24 O6 . 1.207(2) ?
    C24 C25 . 1.475(3) ?
    C25 H25C . 0.9600 ?
    C25 H25B . 0.9600 ?
    C25 H25A . 0.9600 ?
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
    O1 C1 O2 . . 122.29(19) ?
    O1 C1 C2 . . 124.29(17) ?
    O2 C1 C2 . . 113.41(18) ?
    C3 C2 C11 . . 118.92(16) ?
    C3 C2 C1 . . 121.34(16) ?
    C11 C2 C1 . . 119.72(16) ?
    C2 C3 C4 . . 121.66(15) ?
    C2 C3 H3 . . 119.2 ?
    C4 C3 H3 . . 119.2 ?
    C3 C4 C5 . . 121.75(16) ?
    C3 C4 C9 . . 119.03(15) ?
    C5 C4 C9 . . 119.21(17) ?
    C6 C5 C4 . . 121.21(18) ?
    C6 C5 H5 . . 119.4 ?
    C4 C5 H5 . . 119.4 ?
    C5 C6 C7 . . 119.47(19) ?
    C5 C6 H6 . . 120.3 ?
    C7 C6 H6 . . 120.3 ?
    C8 C7 C6 . . 121.6(2) ?
    C8 C7 H7 . . 119.2 ?
    C6 C7 H7 . . 119.2 ?
    C7 C8 C9 . . 120.59(19) ?
    C7 C8 H8 . . 119.7 ?
    C9 C8 H8 . . 119.7 ?
    C8 C9 C10 . . 122.51(15) ?
    C8 C9 C4 . . 117.85(16) ?
    C10 C9 C4 . . 119.63(15) ?
    C11 C10 C9 . . 119.01(14) ?
    C11 C10 C12 . . 120.21(15) ?
    C9 C10 C12 . . 120.78(15) ?
    O3 C11 C10 . . 117.68(14) ?
    O3 C11 C2 . . 120.66(15) ?
    C10 C11 C2 . . 121.66(15) ?
    C13 C12 C21 . . 118.83(15) ?
    C13 C12 C10 . . 120.48(15) ?
    C21 C12 C10 . . 120.69(14) ?
    O4 C13 C12 . . 118.04(15) ?
    O4 C13 C14 . . 120.45(16) ?
    C12 C13 C14 . . 121.51(16) ?
    C15 C14 C13 . . 119.99(17) ?
    C15 C14 H14 . . 120.0 ?
    C13 C14 H14 . . 120.0 ?
    C14 C15 C16 . . 121.38(16) ?
    C14 C15 H15 . . 119.3 ?
    C16 C15 H15 . . 119.3 ?
    C15 C16 C17 . . 122.70(16) ?
    C15 C16 C21 . . 118.82(16) ?
    C17 C16 C21 . . 118.47(16) ?
    C18 C17 C16 . . 121.98(16) ?
    C18 C17 H17 . . 119.0 ?
    C16 C17 H17 . . 119.0 ?
    C17 C18 C19 . . 119.48(17) ?
    C17 C18 H18 . . 120.3 ?
    C19 C18 H18 . . 120.3 ?
    C20 C19 O5 . . 118.59(16) ?
    C20 C19 C18 . . 120.79(17) ?
    O5 C19 C18 . . 120.60(16) ?
    C19 C20 C21 . . 120.81(15) ?
    C19 C20 H20 . . 119.6 ?
    C21 C20 H20 . . 119.6 ?
    C20 C21 C16 . . 118.42(15) ?
    C20 C21 C12 . . 122.17(14) ?
    C16 C21 C12 . . 119.41(15) ?
    O2 C22 H22A . . 109.5 ?
    O2 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    O2 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C1 O2 C22 . . 116.90(19) ?
    C11 O3 H3A . . 109.5 ?
    C13 O4 H4 . . 109.5 ?
    C19 O5 H5A . . 109.5 ?
    C24 C23 H23C . . 109.5 ?
    C24 C23 H23B . . 109.5 ?
    H23C C23 H23B . . 109.5 ?
    C24 C23 H23A . . 109.5 ?
    H23C C23 H23A . . 109.5 ?
    H23B C23 H23A . . 109.5 ?
    O6 C24 C23 . . 122.0(2) ?
    O6 C24 C25 . . 119.93(19) ?
    C23 C24 C25 . . 118.1(2) ?
    C24 C25 H25C . . 109.5 ?
    C24 C25 H25B . . 109.5 ?
    H25C C25 H25B . . 109.5 ?
    C24 C25 H25A . . 109.5 ?
    H25C C25 H25A . . 109.5 ?
    H25B C25 H25A . . 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C1 C2 C3 . . . . -174.9(2) ?
    O2 C1 C2 C3 . . . . 6.4(3) ?
    O1 C1 C2 C11 . . . . 4.2(3) ?
    O2 C1 C2 C11 . . . . -174.54(16) ?
    C11 C2 C3 C4 . . . . 2.6(2) ?
    C1 C2 C3 C4 . . . . -178.31(16) ?
    C2 C3 C4 C5 . . . . 178.99(16) ?
    C2 C3 C4 C9 . . . . -0.4(2) ?
    C3 C4 C5 C6 . . . . -176.50(18) ?
    C9 C4 C5 C6 . . . . 2.9(3) ?
    C4 C5 C6 C7 . . . . -1.5(3) ?
    C5 C6 C7 C8 . . . . -0.7(4) ?
    C6 C7 C8 C9 . . . . 1.3(3) ?
    C7 C8 C9 C10 . . . . 179.01(18) ?
    C7 C8 C9 C4 . . . . 0.1(3) ?
    C3 C4 C9 C8 . . . . 177.26(16) ?
    C5 C4 C9 C8 . . . . -2.1(2) ?
    C3 C4 C9 C10 . . . . -1.7(2) ?
    C5 C4 C9 C10 . . . . 178.91(15) ?
    C8 C9 C10 C11 . . . . -177.46(17) ?
    C4 C9 C10 C11 . . . . 1.4(2) ?
    C8 C9 C10 C12 . . . . 2.5(2) ?
    C4 C9 C10 C12 . . . . -178.56(14) ?
    C9 C10 C11 O3 . . . . -179.32(15) ?
    C12 C10 C11 O3 . . . . 0.7(2) ?
    C9 C10 C11 C2 . . . . 0.8(2) ?
    C12 C10 C11 C2 . . . . -179.15(15) ?
    C3 C2 C11 O3 . . . . 177.27(16) ?
    C1 C2 C11 O3 . . . . -1.8(3) ?
    C3 C2 C11 C10 . . . . -2.9(3) ?
    C1 C2 C11 C10 . . . . 178.04(16) ?
    C11 C10 C12 C13 . . . . -103.2(2) ?
    C9 C10 C12 C13 . . . . 76.8(2) ?
    C11 C10 C12 C21 . . . . 77.1(2) ?
    C9 C10 C12 C21 . . . . -102.88(18) ?
    C21 C12 C13 O4 . . . . -179.95(15) ?
    C10 C12 C13 O4 . . . . 0.4(2) ?
    C21 C12 C13 C14 . . . . 0.6(3) ?
    C10 C12 C13 C14 . . . . -179.07(16) ?
    O4 C13 C14 C15 . . . . 178.50(17) ?
    C12 C13 C14 C15 . . . . -2.1(3) ?
    C13 C14 C15 C16 . . . . 1.4(3) ?
    C14 C15 C16 C17 . . . . 179.77(17) ?
    C14 C15 C16 C21 . . . . 0.7(3) ?
    C15 C16 C17 C18 . . . . -177.50(17) ?
    C21 C16 C17 C18 . . . . 1.5(3) ?
    C16 C17 C18 C19 . . . . 0.1(3) ?
    C17 C18 C19 C20 . . . . -1.7(3) ?
    C17 C18 C19 O5 . . . . 179.80(17) ?
    O5 C19 C20 C21 . . . . -179.78(15) ?
    C18 C19 C20 C21 . . . . 1.7(3) ?
    C19 C20 C21 C16 . . . . -0.1(2) ?
    C19 C20 C21 C12 . . . . 179.65(16) ?
    C15 C16 C21 C20 . . . . 177.55(15) ?
    C17 C16 C21 C20 . . . . -1.5(2) ?
    C15 C16 C21 C12 . . . . -2.2(2) ?
    C17 C16 C21 C12 . . . . 178.77(15) ?
    C13 C12 C21 C20 . . . . -178.21(16) ?
    C10 C12 C21 C20 . . . . 1.5(2) ?
    C13 C12 C21 C16 . . . . 1.5(2) ?
    C10 C12 C21 C16 . . . . -178.83(15) ?
    O1 C1 O2 C22 . . . . 0.5(3) ?
    C2 C1 O2 C22 . . . . 179.2(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
    _geom_hbond_publ_flag
    O5 H5A O6 . 0.82 1.88 2.700(2) 176 yes
    O3 H3A O1 . 0.82 1.88 2.606(2) 148 yes
    O4 H4 O5 4_565 0.82 1.93 2.7466(19) 171 yes
