##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2017-03-28
_journal_date_accepted     2017-04-10
_journal_name_full     'IUCrData'
_journal_year     2017
_journal_volume     2
_journal_issue      4
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314617005351
_journal_coeditor_code     SU4147
_publ_contact_author_name     'Narayanan Uma Maheswari'
_publ_contact_author_address
;
Senior Scientist
Organic & Bio-organic Chemistry
CSIR-Central Leather Research Institute
Adyar, Chennai 600 020
India
;
_publ_contact_author_email     'umanarayanclri@gmail.com'
_publ_contact_author_fax     '044 091 2854 4894'
_publ_contact_author_phone     '044 24437120'
_publ_section_title
;
8-Hydroxy-3,4-bis(4-methoxyphenyl)-1H-isochromen-1-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Sivakalai Mayakrishnan'
;
     Organic & Bio-organic Chemistry
     CSIR Central Leather Research Institute
     Adyar, Chennai 600 020
     India
;
    'Y. Arun'
;
     Organic & Bio-organic Chemistry
     CSIR Central Leather Research Institute
     Adyar, Chennai 600 020
     India
;
    'Narayanan Uma Maheswari'
;    Organic & Bio-organic Chemistry
     CSIR Central Leather Research Institute
     Adyar, Chennai 600 020
     India
;
_publ_section_synopsis
;
The title compound consists of a chromene moiety substituted by two
methoxyphenyl groups and a hydroxy group. The two benzene rings are inclined
to one another by 67.0(2)° and to the mean plane of the 1H-isochromene
ring system by 67.21(16) and 27.61(17)°.
;
data_I
_audit_creation_method     SHELXL-97
_database_code_depnum_ccdc_archive     'CCDC 1540578'
_chemical_name_systematic
;
8-Hydroxy-3,4-bis(4-methoxyphenyl)-1H-isochromen-1-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H18 O5'
_chemical_formula_sum     'C23 H18 O5'
_chemical_formula_iupac     'C23 H18 O5'
_chemical_formula_weight     374.37
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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     5.8882(7)
_cell_length_b     16.418(3)
_cell_length_c     18.894(3)
_cell_angle_alpha     90.00
_cell_angle_beta     95.016(5)
_cell_angle_gamma     90.00
_cell_volume     1819.5(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1375
_cell_measurement_theta_min     2.16
_cell_measurement_theta_max     24.18
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.16
_exptl_crystal_density_diffrn     1.367
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     784
_exptl_absorpt_coefficient_mu     0.096
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_absorpt_correction_T_min     0.9763
_exptl_absorpt_correction_T_max     0.9848
_exptl_special_details     ?
_diffrn_ambient_temperature     296(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 APEXII CCD'
_diffrn_measurement_method     'ω and φ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9449
_diffrn_reflns_av_R_equivalents     0.0677
_diffrn_reflns_av_sigmaI/netI     0.0917
_diffrn_reflns_theta_min     2.16
_diffrn_reflns_theta_max     24.18
_diffrn_reflns_theta_full     24.18
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     4
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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     2910
_reflns_number_gt     1375
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1491
_refine_ls_R_factor_gt     0.0613
_refine_ls_wR_factor_gt     0.1486
_refine_ls_wR_factor_ref     0.1974
_refine_ls_goodness_of_fit_ref     1.010
_refine_ls_restrained_S_all     1.010
_refine_ls_number_reflns     2910
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0901P)²+0.0000P] 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     0.290
_refine_diff_density_min     -0.228
_refine_ls_extinction_method
;
SHELXL97 (Sheldrick, 2008)
;
_refine_ls_extinction_coef     0.006(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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, 2014)
;
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 1.4796(7) 0.1453(3) 0.6993(2) 0.0573(12) Uani d . 1 1 . .
    C C2 1.6348(7) 0.0900(3) 0.6765(2) 0.0606(12) Uani d . 1 1 . .
    H H2 1.7539 0.0716 0.7081 0.073 Uiso calc R 1 1 . .
    C C3 1.6147(6) 0.0621(3) 0.6080(2) 0.0583(12) Uani d . 1 1 . .
    H H3 1.7190 0.0243 0.5936 0.070 Uiso calc R 1 1 . .
    C C4 1.4399(6) 0.0896(2) 0.55963(19) 0.0490(11) Uani d . 1 1 . .
    H H4 1.4289 0.0704 0.5132 0.059 Uiso calc R 1 1 . .
    C C5 1.2825(6) 0.1453(2) 0.58020(18) 0.0423(10) Uani d . 1 1 . .
    C C6 1.1052(6) 0.1788(2) 0.52959(18) 0.0420(10) Uani d . 1 1 . .
    C C7 0.9648(6) 0.2358(3) 0.55146(18) 0.0470(10) Uani d . 1 1 . .
    C C8 1.1367(7) 0.2303(3) 0.6731(2) 0.0594(12) Uani d . 1 1 . .
    C C9 1.3006(6) 0.1729(2) 0.65103(19) 0.0469(10) Uani d . 1 1 . .
    C C10 1.0851(5) 0.1492(2) 0.45471(18) 0.0433(10) Uani d . 1 1 . .
    C C11 1.2498(6) 0.1688(2) 0.40897(19) 0.0483(11) Uani d . 1 1 . .
    H H11 1.3791 0.1975 0.4263 0.058 Uiso calc R 1 1 . .
    C C12 1.2242(6) 0.1464(3) 0.33848(19) 0.0514(11) Uani d . 1 1 . .
    H H12 1.3341 0.1612 0.3084 0.062 Uiso calc R 1 1 . .
    C C13 1.0352(6) 0.1020(3) 0.3123(2) 0.0522(11) Uani d . 1 1 . .
    C C14 0.8745(6) 0.0802(3) 0.3572(2) 0.0586(12) Uani d . 1 1 . .
    H H14 0.7480 0.0499 0.3401 0.070 Uiso calc R 1 1 . .
    C C15 0.9007(6) 0.1033(2) 0.4279(2) 0.0527(11) Uani d . 1 1 . .
    H H15 0.7918 0.0876 0.4580 0.063 Uiso calc R 1 1 . .
    C C16 0.8276(8) 0.0444(4) 0.2115(2) 0.1003(19) Uani d . 1 1 . .
    H H16A 0.8093 -0.0066 0.2352 0.150 Uiso calc R 1 1 . .
    H H16B 0.8410 0.0347 0.1619 0.150 Uiso calc R 1 1 . .
    H H16C 0.6973 0.0783 0.2168 0.150 Uiso calc R 1 1 . .
    C C17 0.7859(6) 0.2841(2) 0.5105(2) 0.0508(11) Uani d . 1 1 . .
    C C18 0.7925(7) 0.3006(3) 0.4386(2) 0.0651(13) Uani d . 1 1 . .
    H H18 0.9111 0.2796 0.4147 0.078 Uiso calc R 1 1 . .
    C C19 0.6284(8) 0.3471(3) 0.4019(3) 0.0772(14) Uani d . 1 1 . .
    H H19 0.6361 0.3570 0.3537 0.093 Uiso calc R 1 1 . .
    C C20 0.4544(8) 0.3789(3) 0.4359(3) 0.0720(14) Uani d . 1 1 . .
    C C21 0.4392(6) 0.3655(3) 0.5068(3) 0.0709(14) Uani d . 1 1 . .
    H H21 0.3202 0.3878 0.5297 0.085 Uiso calc R 1 1 . .
    C C22 0.6072(7) 0.3173(3) 0.5446(2) 0.0628(12) Uani d . 1 1 . .
    H H22 0.5985 0.3076 0.5927 0.075 Uiso calc R 1 1 . .
    C C23 0.1536(9) 0.4761(4) 0.4247(4) 0.126(2) Uani d . 1 1 . .
    H H23A 0.0418 0.4439 0.4461 0.189 Uiso calc R 1 1 . .
    H H23B 0.0787 0.5117 0.3898 0.189 Uiso calc R 1 1 . .
    H H23C 0.2381 0.5079 0.4607 0.189 Uiso calc R 1 1 . .
    O O1 0.9793(4) 0.26094(17) 0.62196(13) 0.0592(8) Uani d . 1 1 . .
    O O2 1.1211(5) 0.2567(2) 0.73262(15) 0.0907(12) Uani d . 1 1 . .
    O O3 1.5022(7) 0.1731(3) 0.76879(19) 0.1251(15) Uani d . 1 1 . .
    H H3A 1.6270 0.1594 0.7878 0.188 Uiso calc R 1 1 . .
    O O4 1.0245(5) 0.08343(19) 0.24135(14) 0.0747(10) Uani d . 1 1 . .
    O O5 0.2996(6) 0.4257(2) 0.3928(2) 0.1062(13) Uani d . 1 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 C2 . 1.383(5) ?
    C1 O3 . 1.386(5) ?
    C1 C9 . 1.407(5) ?
    C2 C3 . 1.369(5) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.391(5) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.382(5) ?
    C4 H4 . 0.9300 ?
    C5 C9 . 1.408(5) ?
    C5 C6 . 1.460(5) ?
    C6 C7 . 1.338(5) ?
    C6 C10 . 1.491(5) ?
    C7 O1 . 1.390(4) ?
    C7 C17 . 1.482(5) ?
    C8 O2 . 1.216(4) ?
    C8 O1 . 1.374(4) ?
    C8 C9 . 1.436(6) ?
    C10 C15 . 1.381(5) ?
    C10 C11 . 1.392(5) ?
    C11 C12 . 1.377(5) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.385(5) ?
    C12 H12 . 0.9300 ?
    C13 O4 . 1.371(4) ?
    C13 C14 . 1.372(5) ?
    C14 C15 . 1.384(5) ?
    C14 H14 . 0.9300 ?
    C15 H15 . 0.9300 ?
    C16 O4 . 1.400(5) ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
    C17 C18 . 1.389(5) ?
    C17 C22 . 1.392(5) ?
    C18 C19 . 1.371(6) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.359(6) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.369(6) ?
    C20 O5 . 1.398(5) ?
    C21 C22 . 1.411(6) ?
    C21 H21 . 0.9300 ?
    C22 H22 . 0.9300 ?
    C23 O5 . 1.370(6) ?
    C23 H23A . 0.9600 ?
    C23 H23B . 0.9600 ?
    C23 H23C . 0.9600 ?
    O3 H3A . 0.8200 ?
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
    C2 C1 O3 . . 119.9(4) ?
    C2 C1 C9 . . 119.2(4) ?
    O3 C1 C9 . . 120.8(4) ?
    C3 C2 C1 . . 120.6(4) ?
    C3 C2 H2 . . 119.7 ?
    C1 C2 H2 . . 119.7 ?
    C2 C3 C4 . . 120.7(4) ?
    C2 C3 H3 . . 119.6 ?
    C4 C3 H3 . . 119.6 ?
    C5 C4 C3 . . 120.4(4) ?
    C5 C4 H4 . . 119.8 ?
    C3 C4 H4 . . 119.8 ?
    C4 C5 C9 . . 118.9(3) ?
    C4 C5 C6 . . 121.6(3) ?
    C9 C5 C6 . . 119.5(3) ?
    C7 C6 C5 . . 119.1(3) ?
    C7 C6 C10 . . 121.4(3) ?
    C5 C6 C10 . . 119.5(3) ?
    C6 C7 O1 . . 121.1(3) ?
    C6 C7 C17 . . 130.0(3) ?
    O1 C7 C17 . . 108.9(3) ?
    O2 C8 O1 . . 114.8(4) ?
    O2 C8 C9 . . 127.5(4) ?
    O1 C8 C9 . . 117.7(4) ?
    C1 C9 C5 . . 120.1(4) ?
    C1 C9 C8 . . 120.5(4) ?
    C5 C9 C8 . . 119.3(3) ?
    C15 C10 C11 . . 117.8(3) ?
    C15 C10 C6 . . 121.4(3) ?
    C11 C10 C6 . . 120.8(3) ?
    C12 C11 C10 . . 121.1(3) ?
    C12 C11 H11 . . 119.5 ?
    C10 C11 H11 . . 119.5 ?
    C11 C12 C13 . . 120.1(3) ?
    C11 C12 H12 . . 119.9 ?
    C13 C12 H12 . . 119.9 ?
    O4 C13 C14 . . 124.8(3) ?
    O4 C13 C12 . . 115.6(3) ?
    C14 C13 C12 . . 119.5(3) ?
    C13 C14 C15 . . 120.0(3) ?
    C13 C14 H14 . . 120.0 ?
    C15 C14 H14 . . 120.0 ?
    C10 C15 C14 . . 121.4(4) ?
    C10 C15 H15 . . 119.3 ?
    C14 C15 H15 . . 119.3 ?
    O4 C16 H16A . . 109.5 ?
    O4 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    O4 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    C18 C17 C22 . . 117.6(4) ?
    C18 C17 C7 . . 122.4(4) ?
    C22 C17 C7 . . 119.9(4) ?
    C19 C18 C17 . . 121.5(4) ?
    C19 C18 H18 . . 119.2 ?
    C17 C18 H18 . . 119.2 ?
    C20 C19 C18 . . 120.2(5) ?
    C20 C19 H19 . . 119.9 ?
    C18 C19 H19 . . 119.9 ?
    C19 C20 C21 . . 121.2(4) ?
    C19 C20 O5 . . 114.6(5) ?
    C21 C20 O5 . . 124.2(5) ?
    C20 C21 C22 . . 118.8(4) ?
    C20 C21 H21 . . 120.6 ?
    C22 C21 H21 . . 120.6 ?
    C17 C22 C21 . . 120.7(4) ?
    C17 C22 H22 . . 119.6 ?
    C21 C22 H22 . . 119.6 ?
    O5 C23 H23A . . 109.5 ?
    O5 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    O5 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C8 O1 C7 . . 123.1(3) ?
    C1 O3 H3A . . 109.5 ?
    C13 O4 C16 . . 117.5(3) ?
    C23 O5 C20 . . 118.6(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
    O3 C1 C2 C3 . . . . -179.9(4) ?
    C9 C1 C2 C3 . . . . -0.2(6) ?
    C1 C2 C3 C4 . . . . 0.9(6) ?
    C2 C3 C4 C5 . . . . -0.4(6) ?
    C3 C4 C5 C9 . . . . -0.8(6) ?
    C3 C4 C5 C6 . . . . 176.4(3) ?
    C4 C5 C6 C7 . . . . -176.4(4) ?
    C9 C5 C6 C7 . . . . 0.8(5) ?
    C4 C5 C6 C10 . . . . 3.2(5) ?
    C9 C5 C6 C10 . . . . -179.6(3) ?
    C5 C6 C7 O1 . . . . -2.8(5) ?
    C10 C6 C7 O1 . . . . 177.6(3) ?
    C5 C6 C7 C17 . . . . 174.4(3) ?
    C10 C6 C7 C17 . . . . -5.3(6) ?
    C2 C1 C9 C5 . . . . -1.0(6) ?
    O3 C1 C9 C5 . . . . 178.8(4) ?
    C2 C1 C9 C8 . . . . -180.0(4) ?
    O3 C1 C9 C8 . . . . -0.3(6) ?
    C4 C5 C9 C1 . . . . 1.4(6) ?
    C6 C5 C9 C1 . . . . -175.8(3) ?
    C4 C5 C9 C8 . . . . -179.5(4) ?
    C6 C5 C9 C8 . . . . 3.2(5) ?
    O2 C8 C9 C1 . . . . -5.2(7) ?
    O1 C8 C9 C1 . . . . 173.9(3) ?
    O2 C8 C9 C5 . . . . 175.8(4) ?
    O1 C8 C9 C5 . . . . -5.2(6) ?
    C7 C6 C10 C15 . . . . -68.8(5) ?
    C5 C6 C10 C15 . . . . 111.6(4) ?
    C7 C6 C10 C11 . . . . 109.6(4) ?
    C5 C6 C10 C11 . . . . -70.0(5) ?
    C15 C10 C11 C12 . . . . 3.0(6) ?
    C6 C10 C11 C12 . . . . -175.5(4) ?
    C10 C11 C12 C13 . . . . -1.6(6) ?
    C11 C12 C13 O4 . . . . 179.4(4) ?
    C11 C12 C13 C14 . . . . -0.3(6) ?
    O4 C13 C14 C15 . . . . -179.0(4) ?
    C12 C13 C14 C15 . . . . 0.7(6) ?
    C11 C10 C15 C14 . . . . -2.6(6) ?
    C6 C10 C15 C14 . . . . 175.8(4) ?
    C13 C14 C15 C10 . . . . 0.8(6) ?
    C6 C7 C17 C18 . . . . -26.0(6) ?
    O1 C7 C17 C18 . . . . 151.4(4) ?
    C6 C7 C17 C22 . . . . 156.4(4) ?
    O1 C7 C17 C22 . . . . -26.2(5) ?
    C22 C17 C18 C19 . . . . -0.6(6) ?
    C7 C17 C18 C19 . . . . -178.3(4) ?
    C17 C18 C19 C20 . . . . 0.4(7) ?
    C18 C19 C20 C21 . . . . 0.2(7) ?
    C18 C19 C20 O5 . . . . 179.5(4) ?
    C19 C20 C21 C22 . . . . -0.5(7) ?
    O5 C20 C21 C22 . . . . -179.7(4) ?
    C18 C17 C22 C21 . . . . 0.3(6) ?
    C7 C17 C22 C21 . . . . 178.0(4) ?
    C20 C21 C22 C17 . . . . 0.2(6) ?
    O2 C8 O1 C7 . . . . -177.5(4) ?
    C9 C8 O1 C7 . . . . 3.4(5) ?
    C6 C7 O1 C8 . . . . 0.7(5) ?
    C17 C7 O1 C8 . . . . -177.0(3) ?
    C14 C13 O4 C16 . . . . 4.8(6) ?
    C12 C13 O4 C16 . . . . -174.9(4) ?
    C19 C20 O5 C23 . . . . -164.1(5) ?
    C21 C20 O5 C23 . . . . 15.2(7) ?
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
    O3 H3A O5 4_766 0.82 2.56 3.236(5) 140
    C18 H18 Cg3 1_555 0.93 2.77 3.494(5) 135
    C3 H3 Cg3 3_856 0.93 2.79 3.611(5) 148
    C11 H11 Cg4 1_655 0.93 2.73 3.593(4) 155
    C23 H23C Cg4 3_666 0.96 3.00 3.872(7) 152
