##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# 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 journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2012-11-28
_journal_date_accepted     2012-11-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      1
_journal_page_first     o54
_journal_page_last     o55
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812049203
_journal_coeditor_code     BT6876
_publ_contact_author_name     'Prof. Charles B. de Koning'
_publ_contact_author_address
;
Molecular Sciences Institute
School of Chemistry
University of the Witwatersrand
PO Wits 2050
Johannesburg
South Africa
;
_publ_contact_author_email     'charles.dekoning@wits.ac.za'
_publ_contact_author_fax     'Int +27 11 717 6749'
_publ_contact_author_phone     'Int +27 11 717 6724'
_publ_section_title
;
(Z)-Ethyl
2-hydroxy-4-oxo-4-(1,4,5,6,8-pentamethoxynaphthalen-2-yl)but-2-enoate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Pillay, Adushan' .
;Molecular Sciences Institute
School of Chemistry
University of the Witwatersrand
PO Wits 2050
Johannesburg
South Africa
;
    'Khorasani, Sanaz' .
;Molecular Sciences Institute
School of Chemistry
University of the Witwatersrand
PO Wits 2050
Johannesburg
South Africa
;
    'de Koning, Charles B.' .
;Molecular Sciences Institute
School of Chemistry
University of the Witwatersrand
PO Wits 2050
Johannesburg
South Africa
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(Z)-Ethyl 2-hydroxy-4-oxo-4-(1,4,5,6,8-pentamethoxynaphthalen-2-yl)but-
2-enoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H24 O9'
_chemical_formula_sum     'C21 H24 O9'
_chemical_formula_iupac     'C21 H24 O9'
_chemical_formula_weight     420.40
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.8019(4)
_cell_length_b     12.3042(6)
_cell_length_c     24.3971(12)
_cell_angle_alpha     100.002(4)
_cell_angle_beta     93.080(4)
_cell_angle_gamma     98.748(4)
_cell_volume     1980.67(18)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1943
_cell_measurement_theta_min     2.62
_cell_measurement_theta_max     25.04
_cell_measurement_temperature     173(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     red
_exptl_crystal_size_max     0.39
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.07
_exptl_crystal_density_diffrn     1.410
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     888
_exptl_absorpt_coefficient_mu     0.111
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details     ?
_diffrn_ambient_temperature     173(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 APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     19594
_diffrn_reflns_av_R_equivalents     0.0830
_diffrn_reflns_av_sigmaI/netI     0.1376
_diffrn_reflns_theta_min     1.70
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -30
_diffrn_reflns_limit_l_max     30
_diffrn_standards_number     0
_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 >
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     7793
_reflns_number_gt     3172
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1518
_refine_ls_R_factor_gt     0.0526
_refine_ls_wR_factor_gt     0.0913
_refine_ls_wR_factor_ref     0.1177
_refine_ls_goodness_of_fit_ref     0.839
_refine_ls_restrained_S_all     0.838
_refine_ls_number_reflns     7793
_refine_ls_number_parameters     572
_refine_ls_number_restraints     54
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0343P)²] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.205
_refine_diff_density_min     -0.247
_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, 2005a)'
_computing_cell_refinement     'SAINT-NT (Bruker, 2005b)'
_computing_data_reduction     'SAINT-NT (Bruker, 2005b)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                'PLATON (Spek, 2009) and SCHAKAL99 (Keller, 1999)'
_computing_publication_material
;
WinGX (Farrugia, 1999) 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 C1A 0.7086(4) 0.6467(2) 0.10802(12) 0.0245(8) Uani d . 1 1 . .
    C C2A 0.7846(4) 0.6053(2) 0.15505(12) 0.0247(8) Uani d . 1 1 . .
    C C3A 0.9780(5) 0.6484(2) 0.18382(13) 0.0274(8) Uani d . 1 1 . .
    C C4A 1.0511(5) 0.6025(2) 0.22628(12) 0.0293(8) Uani d . 1 1 . .
    H H4A 1.1805 0.6317 0.2441 0.035 Uiso calc R 1 1 . .
    C C5A 0.9352(5) 0.5130(3) 0.24321(13) 0.0282(8) Uani d . 1 1 . .
    C C6A 0.7459(5) 0.4692(2) 0.21838(12) 0.0259(8) Uani d . 1 1 . .
    C C7A 0.6673(4) 0.5137(2) 0.17411(12) 0.0244(8) Uani d . 1 1 . .
    C C8A 0.4709(5) 0.4721(3) 0.14548(13) 0.0284(8) Uani d . 1 1 . .
    C C9A 0.4045(5) 0.5152(2) 0.10176(12) 0.0274(8) Uani d . 1 1 . .
    H H9A 0.2747 0.4859 0.0842 0.033 Uiso calc R 1 1 . .
    C C10A 0.5233(4) 0.6030(2) 0.08142(12) 0.0244(8) Uani d . 1 1 . .
    C C11A 0.4404(5) 0.6341(3) 0.03013(13) 0.0269(8) Uani d . 1 1 . .
    C C12A 0.5123(5) 0.7360(3) 0.01041(12) 0.0320(9) Uani d . 1 1 A .
    H H12A 0.6240 0.7863 0.0299 0.038 Uiso calc R 1 1 . .
    C C13A 0.4219(5) 0.7599(3) -0.03533(14) 0.0363(9) Uani d . 1 1 . .
    C C14A 0.4888(6) 0.8667(3) -0.05716(15) 0.0437(9) Uani d PDU 0.880(7) 1 A 1
    C C15A 0.7626(7) 1.0144(3) -0.0550(2) 0.0586(16) Uani d PDU 0.880(7) 1 A 1
    H H15A 0.8505 1.0631 -0.0238 0.070 Uiso calc PR 0.880(7) 1 A 1
    H H15B 0.6543 1.0549 -0.0648 0.070 Uiso calc PR 0.880(7) 1 A 1
    C C16A 0.8787(8) 0.9900(4) -0.1037(2) 0.0657(18) Uani d PDU 0.880(7) 1 A 1
    H H16A 0.9349 1.0602 -0.1150 0.099 Uiso calc PR 0.880(7) 1 A 1
    H H16B 0.7912 0.9425 -0.1347 0.099 Uiso calc PR 0.880(7) 1 A 1
    H H16C 0.9871 0.9510 -0.0938 0.099 Uiso calc PR 0.880(7) 1 A 1
    O O8A 0.6766(4) 0.9106(3) -0.03759(16) 0.0469(10) Uani d PDU 0.880(7) 1 A 1
    O O9A 0.3818(5) 0.9035(3) -0.08750(19) 0.0591(13) Uani d PDU 0.880(7) 1 A 1
    C C14C 0.4888(6) 0.8667(3) -0.05716(15) 0.0437(9) Uani d PD 0.120(7) 1 A 2
    C C15C 0.750(2) 0.971(2) -0.0955(11) 0.035(7) Uiso d PDU 0.120(7) 1 A 2
    H H15E 0.6642 1.0293 -0.0880 0.042 Uiso calc PR 0.120(7) 1 A 2
    H H15F 0.7428 0.9443 -0.1363 0.042 Uiso calc PR 0.120(7) 1 A 2
    C C16C 0.958(4) 1.018(3) -0.0738(15) 0.069(13) Uiso d PDU 0.120(7) 1 A 2
    H H16G 1.0093 1.0779 -0.0934 0.103 Uiso calc PR 0.120(7) 1 A 2
    H H16H 1.0407 0.9587 -0.0799 0.103 Uiso calc PR 0.120(7) 1 A 2
    H H16I 0.9627 1.0477 -0.0338 0.103 Uiso calc PR 0.120(7) 1 A 2
    O O8C 0.6804(13) 0.8774(15) -0.0674(10) 0.046(5) Uiso d PDU 0.120(7) 1 A 2
    O O9C 0.371(3) 0.924(2) -0.0690(15) 0.059(11) Uiso d PDU 0.120(7) 1 A 2
    C C17A 0.9644(5) 0.6896(3) 0.05027(13) 0.0385(9) Uani d . 1 1 . .
    H H17A 1.0490 0.6468 0.0688 0.058 Uiso calc R 1 1 . .
    H H17B 1.0480 0.7528 0.0390 0.058 Uiso calc R 1 1 . .
    H H17C 0.8902 0.6411 0.0171 0.058 Uiso calc R 1 1 . .
    C C18A 1.2844(4) 0.7789(3) 0.19191(13) 0.0377(9) Uani d . 1 1 . .
    H H18A 1.2816 0.8059 0.2320 0.057 Uiso calc R 1 1 . .
    H H18B 1.3455 0.8403 0.1744 0.057 Uiso calc R 1 1 . .
    H H18C 1.3626 0.7179 0.1861 0.057 Uiso calc R 1 1 . .
    C C19A 1.1951(5) 0.5070(3) 0.31297(14) 0.0445(10) Uani d . 1 1 . .
    H H19A 1.2947 0.4988 0.2856 0.067 Uiso calc R 1 1 . .
    H H19B 1.2208 0.4648 0.3424 0.067 Uiso calc R 1 1 . .
    H H19C 1.2034 0.5862 0.3295 0.067 Uiso calc R 1 1 . .
    C C20A 0.6807(5) 0.2757(3) 0.21377(14) 0.0409(9) Uani d . 1 1 . .
    H H20A 0.6351 0.2610 0.1740 0.061 Uiso calc R 1 1 . .
    H H20B 0.6098 0.2179 0.2318 0.061 Uiso calc R 1 1 . .
    H H20C 0.8245 0.2748 0.2180 0.061 Uiso calc R 1 1 . .
    C C21A 0.1682(4) 0.3393(3) 0.13505(13) 0.0371(9) Uani d . 1 1 . .
    H H21A 0.0842 0.3976 0.1362 0.056 Uiso calc R 1 1 . .
    H H21B 0.1033 0.2790 0.1526 0.056 Uiso calc R 1 1 . .
    H H21C 0.1871 0.3094 0.0961 0.056 Uiso calc R 1 1 . .
    O O1A 0.8265(3) 0.73063(16) 0.08806(8) 0.0274(5) Uani d . 1 1 . .
    O O2A 1.0851(3) 0.73912(17) 0.16741(8) 0.0352(6) Uani d . 1 1 . .
    O O3A 0.9989(3) 0.46456(17) 0.28566(9) 0.0378(6) Uani d . 1 1 . .
    O O4A 0.6406(3) 0.38328(17) 0.23943(8) 0.0311(6) Uani d . 1 1 . .
    O O5A 0.3595(3) 0.38650(17) 0.16480(8) 0.0360(6) Uani d . 1 1 . .
    O O6A 0.2923(3) 0.56832(17) 0.00277(8) 0.0317(6) Uani d . 1 1 . .
    O O7A 0.2659(3) 0.6961(2) -0.06553(9) 0.0450(7) Uani d . 1 1 A .
    H H7A 0.2301 0.6399 -0.0510 0.068 Uiso calc R 1 1 . .
    C C1B 0.3209(5) 0.8636(2) 0.39125(12) 0.0268(8) Uani d . 1 1 . .
    C C2B 0.2118(4) 0.9010(3) 0.34798(12) 0.0260(8) Uani d . 1 1 . .
    C C3B 0.0137(5) 0.8495(2) 0.32514(13) 0.0276(8) Uani d . 1 1 . .
    C C4B -0.0842(4) 0.8891(2) 0.28420(12) 0.0282(8) Uani d . 1 1 . .
    H H4B -0.2163 0.8545 0.2704 0.034 Uiso calc R 1 1 . .
    C C5B 0.0082(5) 0.9796(3) 0.26257(13) 0.0285(8) Uani d . 1 1 . .
    C C6B 0.2003(4) 1.0317(2) 0.28214(12) 0.0250(8) Uani d . 1 1 . .
    C C7B 0.3025(4) 0.9964(2) 0.32591(12) 0.0246(8) Uani d . 1 1 . .
    C C8B 0.4976(4) 1.0515(3) 0.35055(12) 0.0274(8) Uani d . 1 1 . .
    C C9B 0.5930(4) 1.0143(2) 0.39183(12) 0.0265(8) Uani d . 1 1 . .
    H H9B 0.7211 1.0531 0.4071 0.032 Uiso calc R 1 1 . .
    C C10B 0.5082(4) 0.9193(3) 0.41316(12) 0.0266(8) Uani d . 1 1 . .
    C C11B 0.6317(5) 0.8932(3) 0.45984(13) 0.0318(8) Uani d . 1 1 . .
    C C12B 0.5872(5) 0.7955(3) 0.48512(12) 0.0317(8) Uani d . 1 1 . .
    H H12B 0.4773 0.7389 0.4701 0.038 Uiso calc R 1 1 . .
    C C13B 0.7032(5) 0.7848(3) 0.53055(13) 0.0315(8) Uani d . 1 1 . .
    C C14B 0.6633(5) 0.6875(3) 0.55955(14) 0.0348(9) Uani d . 1 1 . .
    C C15B 0.4164(5) 0.5460(3) 0.57949(14) 0.0468(10) Uani d . 1 1 . .
    H H15C 0.4399 0.5735 0.6203 0.056 Uiso calc R 1 1 . .
    H H15D 0.4960 0.4857 0.5691 0.056 Uiso calc R 1 1 . .
    C C16B 0.1988(5) 0.5027(3) 0.56370(15) 0.0514(11) Uani d . 1 1 . .
    H H16D 0.1224 0.5640 0.5725 0.077 Uiso calc R 1 1 . .
    H H16E 0.1535 0.4439 0.5847 0.077 Uiso calc R 1 1 . .
    H H16F 0.1785 0.4720 0.5236 0.077 Uiso calc R 1 1 . .
    C C17B 0.1232(5) 0.7820(3) 0.45533(13) 0.0405(9) Uani d . 1 1 . .
    H H17D 0.1955 0.8402 0.4853 0.061 Uiso calc R 1 1 . .
    H H17E 0.0933 0.7116 0.4692 0.061 Uiso calc R 1 1 . .
    H H17F -0.0018 0.8046 0.4432 0.061 Uiso calc R 1 1 . .
    C C18B -0.2757(4) 0.7101(3) 0.32455(13) 0.0366(9) Uani d . 1 1 . .
    H H18D -0.3620 0.7670 0.3323 0.055 Uiso calc R 1 1 . .
    H H18E -0.3215 0.6473 0.3430 0.055 Uiso calc R 1 1 . .
    H H18F -0.2813 0.6834 0.2842 0.055 Uiso calc R 1 1 . .
    C C19B -0.2761(4) 0.9696(3) 0.19809(14) 0.0422(10) Uani d . 1 1 . .
    H H19D -0.2764 0.8902 0.1833 0.063 Uiso calc R 1 1 . .
    H H19E -0.3183 1.0064 0.1680 0.063 Uiso calc R 1 1 . .
    H H19F -0.3686 0.9765 0.2275 0.063 Uiso calc R 1 1 . .
    C C20B 0.2339(5) 1.2213(2) 0.27309(13) 0.0403(9) Uani d . 1 1 . .
    H H20D 0.0885 1.2153 0.2680 0.060 Uiso calc R 1 1 . .
    H H20E 0.2968 1.2743 0.2510 0.060 Uiso calc R 1 1 . .
    H H20F 0.2788 1.2479 0.3127 0.060 Uiso calc R 1 1 . .
    C C21B 0.7722(4) 1.2003(3) 0.35457(13) 0.0387(9) Uani d . 1 1 . .
    H H21D 0.7672 1.2272 0.3946 0.058 Uiso calc R 1 1 . .
    H H21E 0.8154 1.2638 0.3363 0.058 Uiso calc R 1 1 . .
    H H21F 0.8670 1.1476 0.3491 0.058 Uiso calc R 1 1 . .
    O O1B 0.2440(3) 0.76673(16) 0.40899(8) 0.0307(6) Uani d . 1 1 . .
    O O2B -0.0734(3) 0.75818(17) 0.34535(8) 0.0358(6) Uani d . 1 1 . .
    O O3B -0.0784(3) 1.02174(18) 0.22093(9) 0.0380(6) Uani d . 1 1 . .
    O O4B 0.2889(3) 1.11377(17) 0.25499(8) 0.0293(5) Uani d . 1 1 . .
    O O5B 0.5775(3) 1.14496(18) 0.33067(9) 0.0376(6) Uani d . 1 1 . .
    O O6B 0.7876(3) 0.96174(18) 0.47859(9) 0.0434(7) Uani d . 1 1 . .
    O O7B 0.8649(3) 0.85584(19) 0.55340(9) 0.0433(6) Uani d . 1 1 . .
    H H7B 0.8847 0.9086 0.5356 0.065 Uiso calc R 1 1 . .
    O O8B 0.4734(3) 0.63665(18) 0.54955(9) 0.0403(6) Uani d . 1 1 . .
    O O9B 0.7878(4) 0.6589(2) 0.58861(10) 0.0492(7) Uani d . 1 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
    C1A C10A . 1.373(4) ?
    C1A O1A . 1.382(3) ?
    C1A C2A . 1.436(4) ?
    C2A C3A . 1.437(4) ?
    C2A C7A . 1.439(4) ?
    C3A C4A . 1.368(4) ?
    C3A O2A . 1.369(3) ?
    C4A C5A . 1.391(4) ?
    C4A H4A . 0.9500 ?
    C5A O3A . 1.364(3) ?
    C5A C6A . 1.381(4) ?
    C6A O4A . 1.376(3) ?
    C6A C7A . 1.408(4) ?
    C7A C8A . 1.450(4) ?
    C8A C9A . 1.356(4) ?
    C8A O5A . 1.369(3) ?
    C9A C10A . 1.425(4) ?
    C9A H9A . 0.9500 ?
    C10A C11A . 1.479(4) ?
    C11A O6A . 1.268(3) ?
    C11A C12A . 1.446(4) ?
    C12A C13A . 1.343(4) ?
    C12A H12A . 0.9500 ?
    C13A O7A . 1.321(4) ?
    C13A C14A . 1.518(4) ?
    C14A O9A . 1.200(4) ?
    C14A O8A . 1.337(4) ?
    C15A O8A . 1.465(4) ?
    C15A C16A . 1.474(5) ?
    C15A H15A . 0.9900 ?
    C15A H15B . 0.9900 ?
    C16A H16A . 0.9800 ?
    C16A H16B . 0.9800 ?
    C16A H16C . 0.9800 ?
    C15C O8C . 1.470(6) ?
    C15C C16C . 1.478(7) ?
    C15C H15E . 0.9900 ?
    C15C H15F . 0.9900 ?
    C16C H16G . 0.9800 ?
    C16C H16H . 0.9800 ?
    C16C H16I . 0.9800 ?
    C17A O1A . 1.435(3) ?
    C17A H17A . 0.9800 ?
    C17A H17B . 0.9800 ?
    C17A H17C . 0.9800 ?
    C18A O2A . 1.429(3) ?
    C18A H18A . 0.9800 ?
    C18A H18B . 0.9800 ?
    C18A H18C . 0.9800 ?
    C19A O3A . 1.438(3) ?
    C19A H19A . 0.9800 ?
    C19A H19B . 0.9800 ?
    C19A H19C . 0.9800 ?
    C20A O4A . 1.435(3) ?
    C20A H20A . 0.9800 ?
    C20A H20B . 0.9800 ?
    C20A H20C . 0.9800 ?
    C21A O5A . 1.442(3) ?
    C21A H21A . 0.9800 ?
    C21A H21B . 0.9800 ?
    C21A H21C . 0.9800 ?
    O7A H7A . 0.8400 ?
    C1B O1B . 1.377(3) ?
    C1B C10B . 1.383(4) ?
    C1B C2B . 1.437(4) ?
    C2B C3B . 1.436(4) ?
    C2B C7B . 1.444(4) ?
    C3B C4B . 1.369(4) ?
    C3B O2B . 1.370(3) ?
    C4B C5B . 1.393(4) ?
    C4B H4B . 0.9500 ?
    C5B O3B . 1.364(3) ?
    C5B C6B . 1.385(4) ?
    C6B O4B . 1.383(3) ?
    C6B C7B . 1.409(4) ?
    C7B C8B . 1.443(4) ?
    C8B C9B . 1.350(4) ?
    C8B O5B . 1.373(3) ?
    C9B C10B . 1.417(4) ?
    C9B H9B . 0.9500 ?
    C10B C11B . 1.488(4) ?
    C11B O6B . 1.260(3) ?
    C11B C12B . 1.443(4) ?
    C12B C13B . 1.362(4) ?
    C12B H12B . 0.9500 ?
    C13B O7B . 1.326(4) ?
    C13B C14B . 1.492(4) ?
    C14B O9B . 1.207(4) ?
    C14B O8B . 1.337(4) ?
    C15B O8B . 1.453(3) ?
    C15B C16B . 1.500(4) ?
    C15B H15C . 0.9900 ?
    C15B H15D . 0.9900 ?
    C16B H16D . 0.9800 ?
    C16B H16E . 0.9800 ?
    C16B H16F . 0.9800 ?
    C17B O1B . 1.436(3) ?
    C17B H17D . 0.9800 ?
    C17B H17E . 0.9800 ?
    C17B H17F . 0.9800 ?
    C18B O2B . 1.440(3) ?
    C18B H18D . 0.9800 ?
    C18B H18E . 0.9800 ?
    C18B H18F . 0.9800 ?
    C19B O3B . 1.437(3) ?
    C19B H19D . 0.9800 ?
    C19B H19E . 0.9800 ?
    C19B H19F . 0.9800 ?
    C20B O4B . 1.432(3) ?
    C20B H20D . 0.9800 ?
    C20B H20E . 0.9800 ?
    C20B H20F . 0.9800 ?
    C21B O5B . 1.436(3) ?
    C21B H21D . 0.9800 ?
    C21B H21E . 0.9800 ?
    C21B H21F . 0.9800 ?
    O7B H7B . 0.8400 ?
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
    C10A C1A O1A . . 119.0(3) ?
    C10A C1A C2A . . 121.5(3) ?
    O1A C1A C2A . . 119.4(3) ?
    C1A C2A C3A . . 123.2(3) ?
    C1A C2A C7A . . 119.7(3) ?
    C3A C2A C7A . . 117.0(3) ?
    C4A C3A O2A . . 121.4(3) ?
    C4A C3A C2A . . 121.8(3) ?
    O2A C3A C2A . . 116.9(3) ?
    C3A C4A C5A . . 119.8(3) ?
    C3A C4A H4A . . 120.1 ?
    C5A C4A H4A . . 120.1 ?
    O3A C5A C6A . . 116.0(3) ?
    O3A C5A C4A . . 122.5(3) ?
    C6A C5A C4A . . 121.5(3) ?
    O4A C6A C5A . . 117.1(3) ?
    O4A C6A C7A . . 122.8(3) ?
    C5A C6A C7A . . 120.1(3) ?
    C6A C7A C2A . . 119.8(3) ?
    C6A C7A C8A . . 123.7(3) ?
    C2A C7A C8A . . 116.6(3) ?
    C9A C8A O5A . . 122.6(3) ?
    C9A C8A C7A . . 121.5(3) ?
    O5A C8A C7A . . 115.9(3) ?
    C8A C9A C10A . . 122.1(3) ?
    C8A C9A H9A . . 119.0 ?
    C10A C9A H9A . . 119.0 ?
    C1A C10A C9A . . 118.5(3) ?
    C1A C10A C11A . . 125.1(3) ?
    C9A C10A C11A . . 116.3(3) ?
    O6A C11A C12A . . 118.2(3) ?
    O6A C11A C10A . . 117.4(3) ?
    C12A C11A C10A . . 124.4(3) ?
    C13A C12A C11A . . 120.3(3) ?
    C13A C12A H12A . . 119.8 ?
    C11A C12A H12A . . 119.8 ?
    O7A C13A C12A . . 124.9(3) ?
    O7A C13A C14A . . 112.6(3) ?
    C12A C13A C14A . . 122.5(3) ?
    O9A C14A O8A . . 127.0(4) ?
    O9A C14A C13A . . 122.6(4) ?
    O8A C14A C13A . . 110.4(3) ?
    O8A C15A C16A . . 110.4(3) ?
    O8A C15A H15A . . 109.6 ?
    C16A C15A H15A . . 109.6 ?
    O8A C15A H15B . . 109.6 ?
    C16A C15A H15B . . 109.6 ?
    H15A C15A H15B . . 108.1 ?
    C15A C16A H16A . . 109.5 ?
    C15A C16A H16B . . 109.5 ?
    H16A C16A H16B . . 109.5 ?
    C15A C16A H16C . . 109.5 ?
    H16A C16A H16C . . 109.5 ?
    H16B C16A H16C . . 109.5 ?
    C14A O8A C15A . . 116.9(3) ?
    O8C C15C C16C . . 108.3(8) ?
    O8C C15C H15E . . 110.0 ?
    C16C C15C H15E . . 110.0 ?
    O8C C15C H15F . . 110.0 ?
    C16C C15C H15F . . 110.0 ?
    H15E C15C H15F . . 108.4 ?
    C15C C16C H16G . . 109.5 ?
    C15C C16C H16H . . 109.5 ?
    H16G C16C H16H . . 109.5 ?
    C15C C16C H16I . . 109.5 ?
    H16G C16C H16I . . 109.5 ?
    H16H C16C H16I . . 109.5 ?
    O1A C17A H17A . . 109.5 ?
    O1A C17A H17B . . 109.5 ?
    H17A C17A H17B . . 109.5 ?
    O1A C17A H17C . . 109.5 ?
    H17A C17A H17C . . 109.5 ?
    H17B C17A H17C . . 109.5 ?
    O2A C18A H18A . . 109.5 ?
    O2A C18A H18B . . 109.5 ?
    H18A C18A H18B . . 109.5 ?
    O2A C18A H18C . . 109.5 ?
    H18A C18A H18C . . 109.5 ?
    H18B C18A H18C . . 109.5 ?
    O3A C19A H19A . . 109.5 ?
    O3A C19A H19B . . 109.5 ?
    H19A C19A H19B . . 109.5 ?
    O3A C19A H19C . . 109.5 ?
    H19A C19A H19C . . 109.5 ?
    H19B C19A H19C . . 109.5 ?
    O4A C20A H20A . . 109.5 ?
    O4A C20A H20B . . 109.5 ?
    H20A C20A H20B . . 109.5 ?
    O4A C20A H20C . . 109.5 ?
    H20A C20A H20C . . 109.5 ?
    H20B C20A H20C . . 109.5 ?
    O5A C21A H21A . . 109.5 ?
    O5A C21A H21B . . 109.5 ?
    H21A C21A H21B . . 109.5 ?
    O5A C21A H21C . . 109.5 ?
    H21A C21A H21C . . 109.5 ?
    H21B C21A H21C . . 109.5 ?
    C1A O1A C17A . . 113.2(2) ?
    C3A O2A C18A . . 118.5(2) ?
    C5A O3A C19A . . 118.3(2) ?
    C6A O4A C20A . . 112.5(2) ?
    C8A O5A C21A . . 117.1(2) ?
    C13A O7A H7A . . 109.5 ?
    O1B C1B C10B . . 118.9(3) ?
    O1B C1B C2B . . 119.7(3) ?
    C10B C1B C2B . . 121.2(3) ?
    C3B C2B C1B . . 123.8(3) ?
    C3B C2B C7B . . 117.0(3) ?
    C1B C2B C7B . . 119.2(3) ?
    C4B C3B O2B . . 121.0(3) ?
    C4B C3B C2B . . 121.5(3) ?
    O2B C3B C2B . . 117.6(3) ?
    C3B C4B C5B . . 120.5(3) ?
    C3B C4B H4B . . 119.7 ?
    C5B C4B H4B . . 119.7 ?
    O3B C5B C6B . . 115.5(3) ?
    O3B C5B C4B . . 123.7(3) ?
    C6B C5B C4B . . 120.8(3) ?
    O4B C6B C5B . . 117.4(3) ?
    O4B C6B C7B . . 122.3(3) ?
    C5B C6B C7B . . 120.3(3) ?
    C6B C7B C8B . . 123.0(3) ?
    C6B C7B C2B . . 119.8(3) ?
    C8B C7B C2B . . 117.1(3) ?
    C9B C8B O5B . . 122.3(3) ?
    C9B C8B C7B . . 121.5(3) ?
    O5B C8B C7B . . 116.2(3) ?
    C8B C9B C10B . . 122.2(3) ?
    C8B C9B H9B . . 118.9 ?
    C10B C9B H9B . . 118.9 ?
    C1B C10B C9B . . 118.8(3) ?
    C1B C10B C11B . . 126.6(3) ?
    C9B C10B C11B . . 114.6(3) ?
    O6B C11B C12B . . 117.6(3) ?
    O6B C11B C10B . . 117.2(3) ?
    C12B C11B C10B . . 125.2(3) ?
    C13B C12B C11B . . 119.9(3) ?
    C13B C12B H12B . . 120.1 ?
    C11B C12B H12B . . 120.1 ?
    O7B C13B C12B . . 125.3(3) ?
    O7B C13B C14B . . 112.0(3) ?
    C12B C13B C14B . . 122.8(3) ?
    O9B C14B O8B . . 124.5(3) ?
    O9B C14B C13B . . 123.8(3) ?
    O8B C14B C13B . . 111.7(3) ?
    O8B C15B C16B . . 107.3(3) ?
    O8B C15B H15C . . 110.3 ?
    C16B C15B H15C . . 110.3 ?
    O8B C15B H15D . . 110.3 ?
    C16B C15B H15D . . 110.3 ?
    H15C C15B H15D . . 108.5 ?
    C15B C16B H16D . . 109.5 ?
    C15B C16B H16E . . 109.5 ?
    H16D C16B H16E . . 109.5 ?
    C15B C16B H16F . . 109.5 ?
    H16D C16B H16F . . 109.5 ?
    H16E C16B H16F . . 109.5 ?
    O1B C17B H17D . . 109.5 ?
    O1B C17B H17E . . 109.5 ?
    H17D C17B H17E . . 109.5 ?
    O1B C17B H17F . . 109.5 ?
    H17D C17B H17F . . 109.5 ?
    H17E C17B H17F . . 109.5 ?
    O2B C18B H18D . . 109.5 ?
    O2B C18B H18E . . 109.5 ?
    H18D C18B H18E . . 109.5 ?
    O2B C18B H18F . . 109.5 ?
    H18D C18B H18F . . 109.5 ?
    H18E C18B H18F . . 109.5 ?
    O3B C19B H19D . . 109.5 ?
    O3B C19B H19E . . 109.5 ?
    H19D C19B H19E . . 109.5 ?
    O3B C19B H19F . . 109.5 ?
    H19D C19B H19F . . 109.5 ?
    H19E C19B H19F . . 109.5 ?
    O4B C20B H20D . . 109.5 ?
    O4B C20B H20E . . 109.5 ?
    H20D C20B H20E . . 109.5 ?
    O4B C20B H20F . . 109.5 ?
    H20D C20B H20F . . 109.5 ?
    H20E C20B H20F . . 109.5 ?
    O5B C21B H21D . . 109.5 ?
    O5B C21B H21E . . 109.5 ?
    H21D C21B H21E . . 109.5 ?
    O5B C21B H21F . . 109.5 ?
    H21D C21B H21F . . 109.5 ?
    H21E C21B H21F . . 109.5 ?
    C1B O1B C17B . . 114.9(2) ?
    C3B O2B C18B . . 117.6(2) ?
    C5B O3B C19B . . 118.0(2) ?
    C6B O4B C20B . . 113.9(2) ?
    C8B O5B C21B . . 116.8(2) ?
    C13B O7B H7B . . 109.5 ?
    C14B O8B C15B . . 115.7(3) ?
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
    C10A C1A C2A C3A . . . . 179.7(3) ?
    O1A C1A C2A C3A . . . . 1.4(5) ?
    C10A C1A C2A C7A . . . . 1.8(4) ?
    O1A C1A C2A C7A . . . . -176.5(3) ?
    C1A C2A C3A C4A . . . . -175.9(3) ?
    C7A C2A C3A C4A . . . . 2.1(5) ?
    C1A C2A C3A O2A . . . . 5.2(4) ?
    C7A C2A C3A O2A . . . . -176.8(3) ?
    O2A C3A C4A C5A . . . . 177.6(3) ?
    C2A C3A C4A C5A . . . . -1.2(5) ?
    C3A C4A C5A O3A . . . . -179.3(3) ?
    C3A C4A C5A C6A . . . . -0.5(5) ?
    O3A C5A C6A O4A . . . . 1.1(4) ?
    C4A C5A C6A O4A . . . . -177.8(3) ?
    O3A C5A C6A C7A . . . . -179.9(3) ?
    C4A C5A C6A C7A . . . . 1.3(5) ?
    O4A C6A C7A C2A . . . . 178.7(3) ?
    C5A C6A C7A C2A . . . . -0.3(5) ?
    O4A C6A C7A C8A . . . . -1.5(5) ?
    C5A C6A C7A C8A . . . . 179.5(3) ?
    C1A C2A C7A C6A . . . . 176.7(3) ?
    C3A C2A C7A C6A . . . . -1.3(4) ?
    C1A C2A C7A C8A . . . . -3.1(4) ?
    C3A C2A C7A C8A . . . . 178.9(3) ?
    C6A C7A C8A C9A . . . . -177.7(3) ?
    C2A C7A C8A C9A . . . . 2.1(4) ?
    C6A C7A C8A O5A . . . . 1.5(4) ?
    C2A C7A C8A O5A . . . . -178.7(3) ?
    O5A C8A C9A C10A . . . . -178.9(3) ?
    C7A C8A C9A C10A . . . . 0.2(5) ?
    O1A C1A C10A C9A . . . . 178.9(3) ?
    C2A C1A C10A C9A . . . . 0.6(4) ?
    O1A C1A C10A C11A . . . . 3.6(5) ?
    C2A C1A C10A C11A . . . . -174.8(3) ?
    C8A C9A C10A C1A . . . . -1.6(5) ?
    C8A C9A C10A C11A . . . . 174.2(3) ?
    C1A C10A C11A O6A . . . . 162.6(3) ?
    C9A C10A C11A O6A . . . . -12.9(4) ?
    C1A C10A C11A C12A . . . . -19.7(5) ?
    C9A C10A C11A C12A . . . . 164.8(3) ?
    O6A C11A C12A C13A . . . . 0.7(5) ?
    C10A C11A C12A C13A . . . . -177.0(3) ?
    C11A C12A C13A O7A . . . . 0.0(5) ?
    C11A C12A C13A C14A . . . . 178.8(3) ?
    O7A C13A C14A O9A . . . . 19.6(6) ?
    C12A C13A C14A O9A . . . . -159.3(4) ?
    O7A C13A C14A O8A . . . . -160.7(3) ?
    C12A C13A C14A O8A . . . . 20.4(5) ?
    O9A C14A O8A C15A . . . . -0.3(7) ?
    C13A C14A O8A C15A . . . . -180.0(3) ?
    C16A C15A O8A C14A . . . . -95.6(5) ?
    C10A C1A O1A C17A . . . . -94.7(3) ?
    C2A C1A O1A C17A . . . . 83.7(3) ?
    C4A C3A O2A C18A . . . . 6.0(4) ?
    C2A C3A O2A C18A . . . . -175.1(3) ?
    C6A C5A O3A C19A . . . . 180.0(3) ?
    C4A C5A O3A C19A . . . . -1.2(4) ?
    C5A C6A O4A C20A . . . . -87.5(3) ?
    C7A C6A O4A C20A . . . . 93.5(3) ?
    C9A C8A O5A C21A . . . . 2.6(4) ?
    C7A C8A O5A C21A . . . . -176.6(3) ?
    O1B C1B C2B C3B . . . . 6.8(5) ?
    C10B C1B C2B C3B . . . . -177.4(3) ?
    O1B C1B C2B C7B . . . . -174.0(3) ?
    C10B C1B C2B C7B . . . . 1.9(4) ?
    C1B C2B C3B C4B . . . . 179.5(3) ?
    C7B C2B C3B C4B . . . . 0.2(5) ?
    C1B C2B C3B O2B . . . . -1.3(5) ?
    C7B C2B C3B O2B . . . . 179.4(3) ?
    O2B C3B C4B C5B . . . . -177.8(3) ?
    C2B C3B C4B C5B . . . . 1.4(5) ?
    C3B C4B C5B O3B . . . . 178.5(3) ?
    C3B C4B C5B C6B . . . . -0.3(5) ?
    O3B C5B C6B O4B . . . . -4.9(4) ?
    C4B C5B C6B O4B . . . . 173.9(3) ?
    O3B C5B C6B C7B . . . . 178.7(3) ?
    C4B C5B C6B C7B . . . . -2.5(5) ?
    O4B C6B C7B C8B . . . . 7.8(5) ?
    C5B C6B C7B C8B . . . . -176.0(3) ?
    O4B C6B C7B C2B . . . . -172.2(3) ?
    C5B C6B C7B C2B . . . . 4.0(4) ?
    C3B C2B C7B C6B . . . . -2.9(4) ?
    C1B C2B C7B C6B . . . . 177.8(3) ?
    C3B C2B C7B C8B . . . . 177.2(3) ?
    C1B C2B C7B C8B . . . . -2.1(4) ?
    C6B C7B C8B C9B . . . . -178.8(3) ?
    C2B C7B C8B C9B . . . . 1.1(4) ?
    C6B C7B C8B O5B . . . . 2.8(4) ?
    C2B C7B C8B O5B . . . . -177.2(3) ?
    O5B C8B C9B C10B . . . . 178.5(3) ?
    C7B C8B C9B C10B . . . . 0.3(5) ?
    O1B C1B C10B C9B . . . . 175.4(3) ?
    C2B C1B C10B C9B . . . . -0.5(5) ?
    O1B C1B C10B C11B . . . . -7.6(5) ?
    C2B C1B C10B C11B . . . . 176.5(3) ?
    C8B C9B C10B C1B . . . . -0.6(5) ?
    C8B C9B C10B C11B . . . . -178.0(3) ?
    C1B C10B C11B O6B . . . . -171.3(3) ?
    C9B C10B C11B O6B . . . . 5.8(4) ?
    C1B C10B C11B C12B . . . . 8.8(5) ?
    C9B C10B C11B C12B . . . . -174.0(3) ?
    O6B C11B C12B C13B . . . . 5.3(5) ?
    C10B C11B C12B C13B . . . . -174.9(3) ?
    C11B C12B C13B O7B . . . . -3.2(5) ?
    C11B C12B C13B C14B . . . . 178.6(3) ?
    O7B C13B C14B O9B . . . . -20.1(5) ?
    C12B C13B C14B O9B . . . . 158.3(3) ?
    O7B C13B C14B O8B . . . . 159.6(3) ?
    C12B C13B C14B O8B . . . . -21.9(4) ?
    C10B C1B O1B C17B . . . . 92.4(3) ?
    C2B C1B O1B C17B . . . . -91.6(3) ?
    C4B C3B O2B C18B . . . . -3.9(4) ?
    C2B C3B O2B C18B . . . . 176.9(3) ?
    C6B C5B O3B C19B . . . . 178.7(3) ?
    C4B C5B O3B C19B . . . . -0.1(5) ?
    C5B C6B O4B C20B . . . . 82.7(3) ?
    C7B C6B O4B C20B . . . . -101.0(3) ?
    C9B C8B O5B C21B . . . . 2.1(4) ?
    C7B C8B O5B C21B . . . . -179.6(3) ?
    O9B C14B O8B C15B . . . . 4.2(5) ?
    C13B C14B O8B C15B . . . . -175.5(3) ?
    C16B C15B O8B C14B . . . . 178.6(3) ?
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
    O7A H7A O6A . 0.84 1.77 2.499(3) 144 yes
    O7B H7B O6B . 0.84 1.77 2.497(3) 143 yes
    C17B H17D O6B 2_676 0.98 2.43 3.234(4) 139 yes
    C19A H19B O9B 2_766 0.98 2.45 3.419(4) 168 yes
    C19B H19E O9A 2_575 0.98 2.47 3.440(5) 172 yes
    C20A H20B O4B 1_545 0.98 2.50 3.384(4) 150 yes
    C20B H20E O4A 1_565 0.98 2.57 3.382(4) 140 yes
    C20B H20F O9B 2_676 0.98 2.58 3.460(4) 150 yes
    C18A H18A Cg3 1_655 0.98 2.66 3.486(3) 142 yes
    C18A H18C Cg1 1_655 0.98 2.92 3.844(3) 158 yes
    C18B H18F Cg2 1_455 0.98 2.66 3.522(3) 147 yes
    C21A H21A Cg2 1_455 0.98 2.96 3.845(3) 150 yes
