##############################################################################
###                                                                        ###
###        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           #
# 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     2009-03-09
_journal_date_accepted     2009-03-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      4
_journal_page_first     o776
_journal_page_last     o777
_journal_paper_category     QO
_journal_coeditor_code     LH2786
_publ_contact_author_name     'Prof. Fun, Hoong-Kun'
_publ_contact_author_address
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      MALAYSIA
;
_publ_contact_author_email     hkfun@usm.my
_publ_contact_author_fax     '6 04 6579150'
_publ_contact_author_phone     '6 04 6533652'
_publ_section_title
;\
6,6'-Diethoxy-2,2'-[4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]\
diphenol--ethanol--water (1/1/1)
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Kargar, Hadi' ?
;     Department of Chemistry,
      School of Science,
      Payame Noor University (PNU),
      Ardakan, Yazd,
      Iran
;
    'Kia, Reza'
;
      Additional correspondance author, e-mail: zsrkk@yahoo.com.
;
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Jamshidvand, Arezoo' ?
;     Department of Chemistry,
      School of Science,
      Payame Noor University (PNU),
      Ardakan, Yazd,
      Iran
;
    'Fun, Hoong-Kun' ?
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
6,6'-Diethoxy-2,2'-[4,5-dimethyl-o-
phenylenebis(nitrilomethylidyne)]diphenol--ethanol--water (1/1/1)
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C26 H28 N2 O4, C2 H6 O, H2 O'
_chemical_formula_sum     'C28 H36 N2 O6'
_chemical_formula_iupac     'C26 H28 N2 O4, C2 H6 O, H2 O'
_chemical_formula_weight     496.59
_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     9.5095(5)
_cell_length_b     25.6633(12)
_cell_length_c     10.7766(5)
_cell_angle_alpha     90.00
_cell_angle_beta     99.177(2)
_cell_angle_gamma     90.00
_cell_volume     2596.3(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4281
_cell_measurement_theta_min     2.31
_cell_measurement_theta_max     27.23
_cell_measurement_temperature     100
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'orange'
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.02
_exptl_crystal_density_diffrn     1.270
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1064
_exptl_absorpt_coefficient_mu     0.089
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.9610
_exptl_absorpt_correction_T_max     0.9985
_exptl_special_details
;
The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra
open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0(1) K.
;
_diffrn_ambient_temperature     100
_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 area-detector
;
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     32813
_diffrn_reflns_av_R_equivalents     0.0681
_diffrn_reflns_av_sigmaI/netI     0.0778
_diffrn_reflns_theta_min     2.31
_diffrn_reflns_theta_max     30.09
_diffrn_reflns_theta_full     30.09
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -36
_diffrn_reflns_limit_k_max     32
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     15
_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 > 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     7595
_reflns_number_gt     4303
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1311
_refine_ls_R_factor_gt     0.0659
_refine_ls_wR_factor_gt     0.1347
_refine_ls_wR_factor_ref     0.1596
_refine_ls_goodness_of_fit_ref     1.030
_refine_ls_restrained_S_all     1.030
_refine_ls_number_reflns     7595
_refine_ls_number_parameters     341
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0637P)²+0.5228P] 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     0.379
_refine_diff_density_min     -0.514
_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'
    'N' 'N' 0.0061 0.0033
                         '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, 2005)'
_computing_cell_refinement     'SAINT (Bruker, 2005)'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (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_disorder_assembly
    _atom_site_disorder_group
    O O1 -0.06040(14) 0.16561(5) 0.35336(13) 0.0257(3) Uani d . 1 . .
    H H1 0.0253 0.1707 0.3841 0.039 Uiso calc R 1 . .
    O O2 0.13555(14) 0.07045(5) 0.28857(12) 0.0261(3) Uani d . 1 . .
    H H2 0.1782 0.0973 0.3193 0.039 Uiso calc R 1 . .
    O O3 -0.33019(13) 0.16242(5) 0.25794(12) 0.0250(3) Uani d . 1 . .
    O O4 -0.00004(14) -0.01584(5) 0.22724(12) 0.0276(3) Uani d . 1 . .
    O O5 0.1829(2) 0.38301(7) 0.43926(18) 0.0696(7) Uani d . 1 . .
    H H5 0.2336 0.3938 0.5052 0.104 Uiso calc R 1 . .
    N N1 0.16852(16) 0.21898(6) 0.42494(13) 0.0202(3) Uani d . 1 . .
    N N2 0.30447(16) 0.12535(6) 0.45335(14) 0.0221(4) Uani d . 1 . .
    C C1 -0.12615(19) 0.21183(7) 0.32673(16) 0.0195(4) Uani d . 1 . .
    C C2 -0.2720(2) 0.21128(7) 0.27477(17) 0.0212(4) Uani d . 1 . .
    C C3 -0.3428(2) 0.25763(8) 0.24528(17) 0.0239(4) Uani d . 1 . .
    H H3A -0.4410 0.2573 0.2103 0.029 Uiso calc R 1 . .
    C C4 -0.2710(2) 0.30517(8) 0.26650(18) 0.0271(5) Uani d . 1 . .
    H H4A -0.3207 0.3369 0.2456 0.032 Uiso calc R 1 . .
    C C5 -0.1292(2) 0.30622(8) 0.31737(17) 0.0241(4) Uani d . 1 . .
    H H5A -0.0812 0.3387 0.3319 0.029 Uiso calc R 1 . .
    C C6 -0.0546(2) 0.25953(7) 0.34807(16) 0.0197(4) Uani d . 1 . .
    C C7 0.0960(2) 0.26133(8) 0.39833(16) 0.0216(4) Uani d . 1 . .
    H H7A 0.1422 0.2941 0.4120 0.026 Uiso calc R 1 . .
    C C8 0.31619(19) 0.21948(7) 0.47186(16) 0.0195(4) Uani d . 1 . .
    C C9 0.3962(2) 0.26478(8) 0.50515(17) 0.0222(4) Uani d . 1 . .
    H H9A 0.3501 0.2977 0.4944 0.027 Uiso calc R 1 . .
    C C10 0.5406(2) 0.26294(7) 0.55340(16) 0.0212(4) Uani d . 1 . .
    C C11 0.6084(2) 0.21406(8) 0.56871(17) 0.0216(4) Uani d . 1 . .
    C C12 0.5301(2) 0.16936(8) 0.53558(16) 0.0222(4) Uani d . 1 . .
    H H12A 0.5768 0.1365 0.5447 0.027 Uiso calc R 1 . .
    C C13 0.3845(2) 0.17112(7) 0.48914(16) 0.0207(4) Uani d . 1 . .
    C C14 0.3273(2) 0.08414(7) 0.52055(17) 0.0236(4) Uani d . 1 . .
    H H14A 0.3939 0.0857 0.5962 0.028 Uiso calc R 1 . .
    C C15 0.2554(2) 0.03506(8) 0.48551(17) 0.0229(4) Uani d . 1 . .
    C C16 0.2757(2) -0.00817(8) 0.56692(18) 0.0279(5) Uani d . 1 . .
    H H16A 0.3398 -0.0056 0.6439 0.033 Uiso calc R 1 . .
    C C17 0.2041(2) -0.05394(8) 0.53627(19) 0.0287(5) Uani d . 1 . .
    H H17A 0.2191 -0.0829 0.5917 0.034 Uiso calc R 1 . .
    C C18 0.1087(2) -0.05798(8) 0.42326(19) 0.0270(4) Uani d . 1 . .
    H H18A 0.0579 -0.0895 0.4029 0.032 Uiso calc R 1 . .
    C C19 0.0884(2) -0.01644(7) 0.34162(17) 0.0232(4) Uani d . 1 . .
    C C20 0.16074(19) 0.03062(7) 0.37184(17) 0.0208(4) Uani d . 1 . .
    C C21 -0.47745(19) 0.15886(8) 0.20175(18) 0.0262(4) Uani d . 1 . .
    H H21A -0.4913 0.1729 0.1151 0.031 Uiso calc R 1 . .
    H H21B -0.5377 0.1790 0.2515 0.031 Uiso calc R 1 . .
    C C22 -0.5166(2) 0.10202(8) 0.20022(19) 0.0310(5) Uani d . 1 . .
    H H22A -0.6166 0.0978 0.1622 0.047 Uiso calc R 1 . .
    H H22B -0.5027 0.0887 0.2865 0.047 Uiso calc R 1 . .
    H H22C -0.4559 0.0826 0.1510 0.047 Uiso calc R 1 . .
    C C23 -0.0850(2) -0.06146(8) 0.1942(2) 0.0305(5) Uani d . 1 . .
    H H23A -0.1449 -0.0689 0.2592 0.037 Uiso calc R 1 . .
    H H23B -0.0231 -0.0920 0.1869 0.037 Uiso calc R 1 . .
    C C24 -0.1771(3) -0.05042(9) 0.0699(2) 0.0410(6) Uani d . 1 . .
    H H24A -0.2390 -0.0804 0.0451 0.061 Uiso calc R 1 . .
    H H24B -0.1166 -0.0441 0.0059 0.061 Uiso calc R 1 . .
    H H24C -0.2358 -0.0196 0.0778 0.061 Uiso calc R 1 . .
    C C25 0.6220(2) 0.31263(8) 0.58803(19) 0.0276(5) Uani d . 1 . .
    H H25A 0.5559 0.3422 0.5782 0.041 Uiso calc R 1 . .
    H H25B 0.6935 0.3174 0.5328 0.041 Uiso calc R 1 . .
    H H25C 0.6694 0.3106 0.6756 0.041 Uiso calc R 1 . .
    C C26 0.7651(2) 0.21015(8) 0.62075(18) 0.0279(5) Uani d . 1 . .
    H H26A 0.7960 0.1738 0.6173 0.042 Uiso calc R 1 . .
    H H26B 0.7816 0.2222 0.7082 0.042 Uiso calc R 1 . .
    H H26C 0.8195 0.2319 0.5705 0.042 Uiso calc R 1 . .
    C C27 0.0836(4) 0.45876(12) 0.3369(3) 0.0799(11) Uani d . 1 . .
    H H27A 0.0918 0.4816 0.2655 0.120 Uiso calc R 1 . .
    H H27B 0.0995 0.4791 0.4148 0.120 Uiso calc R 1 . .
    H H27C -0.0118 0.4433 0.3258 0.120 Uiso calc R 1 . .
    C C28 0.1892(3) 0.41771(13) 0.3437(2) 0.0575(8) Uani d . 1 . .
    H H28A 0.1756 0.3986 0.2629 0.069 Uiso calc R 1 . .
    H H28B 0.2852 0.4337 0.3553 0.069 Uiso calc R 1 . .
    O O1W 0.84548(19) 0.08448(7) 0.14875(16) 0.0412(4) Uani d . 1 . .
    H H1W1 0.920(3) 0.0656(11) 0.169(3) 0.064(9) Uiso d . 1 . .
    H H2W1 0.855(3) 0.1065(13) 0.199(3) 0.076(11) Uiso 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
    O1 C1 . 1.350(2) ?
    O1 H1 . 0.8400 ?
    O2 C20 . 1.356(2) ?
    O2 H2 . 0.8400 ?
    O3 C2 . 1.371(2) ?
    O3 C21 . 1.437(2) ?
    O4 C19 . 1.377(2) ?
    O4 C23 . 1.435(2) ?
    O5 C28 . 1.370(3) ?
    O5 H5 . 0.8400 ?
    N1 C7 . 1.295(2) ?
    N1 C8 . 1.415(2) ?
    N2 C14 . 1.281(2) ?
    N2 C13 . 1.419(2) ?
    C1 C6 . 1.402(3) ?
    C1 C2 . 1.411(2) ?
    C2 C3 . 1.379(3) ?
    C3 C4 . 1.399(3) ?
    C3 H3A . 0.9500 ?
    C4 C5 . 1.373(3) ?
    C4 H4A . 0.9500 ?
    C5 C6 . 1.405(3) ?
    C5 H5A . 0.9500 ?
    C6 C7 . 1.448(3) ?
    C7 H7A . 0.9500 ?
    C8 C13 . 1.399(3) ?
    C8 C9 . 1.404(3) ?
    C9 C10 . 1.390(3) ?
    C9 H9A . 0.9500 ?
    C10 C11 . 1.408(3) ?
    C10 C25 . 1.507(3) ?
    C11 C12 . 1.383(3) ?
    C11 C26 . 1.510(3) ?
    C12 C13 . 1.396(3) ?
    C12 H12A . 0.9500 ?
    C14 C15 . 1.454(3) ?
    C14 H14A . 0.9500 ?
    C15 C20 . 1.404(2) ?
    C15 C16 . 1.409(3) ?
    C16 C17 . 1.372(3) ?
    C16 H16A . 0.9500 ?
    C17 C18 . 1.401(3) ?
    C17 H17A . 0.9500 ?
    C18 C19 . 1.376(3) ?
    C18 H18A . 0.9500 ?
    C19 C20 . 1.403(3) ?
    C21 C22 . 1.505(3) ?
    C21 H21A . 0.9900 ?
    C21 H21B . 0.9900 ?
    C22 H22A . 0.9800 ?
    C22 H22B . 0.9800 ?
    C22 H22C . 0.9800 ?
    C23 C24 . 1.506(3) ?
    C23 H23A . 0.9900 ?
    C23 H23B . 0.9900 ?
    C24 H24A . 0.9800 ?
    C24 H24B . 0.9800 ?
    C24 H24C . 0.9800 ?
    C25 H25A . 0.9800 ?
    C25 H25B . 0.9800 ?
    C25 H25C . 0.9800 ?
    C26 H26A . 0.9800 ?
    C26 H26B . 0.9800 ?
    C26 H26C . 0.9800 ?
    C27 C28 . 1.449(4) ?
    C27 H27A . 0.9800 ?
    C27 H27B . 0.9800 ?
    C27 H27C . 0.9800 ?
    C28 H28A . 0.9900 ?
    C28 H28B . 0.9900 ?
    O1W H1W1 . 0.86(3) ?
    O1W H2W1 . 0.78(3) ?
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 O1 H1 . . 109.5 ?
    C20 O2 H2 . . 109.5 ?
    C2 O3 C21 . . 117.35(14) ?
    C19 O4 C23 . . 116.90(15) ?
    C28 O5 H5 . . 109.5 ?
    C7 N1 C8 . . 122.35(16) ?
    C14 N2 C13 . . 119.64(15) ?
    O1 C1 C6 . . 122.41(16) ?
    O1 C1 C2 . . 117.93(16) ?
    C6 C1 C2 . . 119.66(17) ?
    O3 C2 C3 . . 125.94(17) ?
    O3 C2 C1 . . 114.33(16) ?
    C3 C2 C1 . . 119.73(18) ?
    C2 C3 C4 . . 120.48(17) ?
    C2 C3 H3A . . 119.8 ?
    C4 C3 H3A . . 119.8 ?
    C5 C4 C3 . . 120.33(18) ?
    C5 C4 H4A . . 119.8 ?
    C3 C4 H4A . . 119.8 ?
    C4 C5 C6 . . 120.30(18) ?
    C4 C5 H5A . . 119.9 ?
    C6 C5 H5A . . 119.9 ?
    C1 C6 C5 . . 119.50(17) ?
    C1 C6 C7 . . 120.96(17) ?
    C5 C6 C7 . . 119.52(17) ?
    N1 C7 C6 . . 121.07(17) ?
    N1 C7 H7A . . 119.5 ?
    C6 C7 H7A . . 119.5 ?
    C13 C8 C9 . . 118.63(17) ?
    C13 C8 N1 . . 116.93(16) ?
    C9 C8 N1 . . 124.41(17) ?
    C10 C9 C8 . . 122.02(18) ?
    C10 C9 H9A . . 119.0 ?
    C8 C9 H9A . . 119.0 ?
    C9 C10 C11 . . 118.72(17) ?
    C9 C10 C25 . . 120.09(18) ?
    C11 C10 C25 . . 121.19(17) ?
    C12 C11 C10 . . 119.47(17) ?
    C12 C11 C26 . . 119.94(18) ?
    C10 C11 C26 . . 120.59(17) ?
    C11 C12 C13 . . 121.84(18) ?
    C11 C12 H12A . . 119.1 ?
    C13 C12 H12A . . 119.1 ?
    C12 C13 C8 . . 119.30(17) ?
    C12 C13 N2 . . 121.93(17) ?
    C8 C13 N2 . . 118.71(16) ?
    N2 C14 C15 . . 122.55(17) ?
    N2 C14 H14A . . 118.7 ?
    C15 C14 H14A . . 118.7 ?
    C20 C15 C16 . . 118.99(17) ?
    C20 C15 C14 . . 120.42(17) ?
    C16 C15 C14 . . 120.55(17) ?
    C17 C16 C15 . . 120.73(18) ?
    C17 C16 H16A . . 119.6 ?
    C15 C16 H16A . . 119.6 ?
    C16 C17 C18 . . 120.03(18) ?
    C16 C17 H17A . . 120.0 ?
    C18 C17 H17A . . 120.0 ?
    C19 C18 C17 . . 120.25(18) ?
    C19 C18 H18A . . 119.9 ?
    C17 C18 H18A . . 119.9 ?
    C18 C19 O4 . . 125.77(17) ?
    C18 C19 C20 . . 120.33(17) ?
    O4 C19 C20 . . 113.90(16) ?
    O2 C20 C19 . . 117.85(16) ?
    O2 C20 C15 . . 122.49(17) ?
    C19 C20 C15 . . 119.67(17) ?
    O3 C21 C22 . . 106.80(16) ?
    O3 C21 H21A . . 110.4 ?
    C22 C21 H21A . . 110.4 ?
    O3 C21 H21B . . 110.4 ?
    C22 C21 H21B . . 110.4 ?
    H21A C21 H21B . . 108.6 ?
    C21 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C21 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    O4 C23 C24 . . 107.00(17) ?
    O4 C23 H23A . . 110.3 ?
    C24 C23 H23A . . 110.3 ?
    O4 C23 H23B . . 110.3 ?
    C24 C23 H23B . . 110.3 ?
    H23A C23 H23B . . 108.6 ?
    C23 C24 H24A . . 109.5 ?
    C23 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    C23 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    C10 C25 H25A . . 109.5 ?
    C10 C25 H25B . . 109.5 ?
    H25A C25 H25B . . 109.5 ?
    C10 C25 H25C . . 109.5 ?
    H25A C25 H25C . . 109.5 ?
    H25B C25 H25C . . 109.5 ?
    C11 C26 H26A . . 109.5 ?
    C11 C26 H26B . . 109.5 ?
    H26A C26 H26B . . 109.5 ?
    C11 C26 H26C . . 109.5 ?
    H26A C26 H26C . . 109.5 ?
    H26B C26 H26C . . 109.5 ?
    C28 C27 H27A . . 109.5 ?
    C28 C27 H27B . . 109.5 ?
    H27A C27 H27B . . 109.5 ?
    C28 C27 H27C . . 109.5 ?
    H27A C27 H27C . . 109.5 ?
    H27B C27 H27C . . 109.5 ?
    O5 C28 C27 . . 113.5(3) ?
    O5 C28 H28A . . 108.9 ?
    C27 C28 H28A . . 108.9 ?
    O5 C28 H28B . . 108.9 ?
    C27 C28 H28B . . 108.9 ?
    H28A C28 H28B . . 107.7 ?
    H1W1 O1W H2W1 . . 103(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
    C21 O3 C2 C3 . . . . 1.6(3) ?
    C21 O3 C2 C1 . . . . -178.13(16) ?
    O1 C1 C2 O3 . . . . 0.3(2) ?
    C6 C1 C2 O3 . . . . 179.82(16) ?
    O1 C1 C2 C3 . . . . -179.47(16) ?
    C6 C1 C2 C3 . . . . 0.1(3) ?
    O3 C2 C3 C4 . . . . -179.69(17) ?
    C1 C2 C3 C4 . . . . 0.0(3) ?
    C2 C3 C4 C5 . . . . -0.2(3) ?
    C3 C4 C5 C6 . . . . 0.3(3) ?
    O1 C1 C6 C5 . . . . 179.54(16) ?
    C2 C1 C6 C5 . . . . 0.0(3) ?
    O1 C1 C6 C7 . . . . 1.1(3) ?
    C2 C1 C6 C7 . . . . -178.44(17) ?
    C4 C5 C6 C1 . . . . -0.2(3) ?
    C4 C5 C6 C7 . . . . 178.27(18) ?
    C8 N1 C7 C6 . . . . 178.76(16) ?
    C1 C6 C7 N1 . . . . 0.0(3) ?
    C5 C6 C7 N1 . . . . -178.43(17) ?
    C7 N1 C8 C13 . . . . -175.89(16) ?
    C7 N1 C8 C9 . . . . 6.1(3) ?
    C13 C8 C9 C10 . . . . 0.6(3) ?
    N1 C8 C9 C10 . . . . 178.60(17) ?
    C8 C9 C10 C11 . . . . 0.2(3) ?
    C8 C9 C10 C25 . . . . -179.88(17) ?
    C9 C10 C11 C12 . . . . 0.0(3) ?
    C25 C10 C11 C12 . . . . -179.86(17) ?
    C9 C10 C11 C26 . . . . 179.99(17) ?
    C25 C10 C11 C26 . . . . 0.1(3) ?
    C10 C11 C12 C13 . . . . -1.2(3) ?
    C26 C11 C12 C13 . . . . 178.89(17) ?
    C11 C12 C13 C8 . . . . 2.0(3) ?
    C11 C12 C13 N2 . . . . 179.06(17) ?
    C9 C8 C13 C12 . . . . -1.7(3) ?
    N1 C8 C13 C12 . . . . -179.82(16) ?
    C9 C8 C13 N2 . . . . -178.84(16) ?
    N1 C8 C13 N2 . . . . 3.0(2) ?
    C14 N2 C13 C12 . . . . 40.6(3) ?
    C14 N2 C13 C8 . . . . -142.33(18) ?
    C13 N2 C14 C15 . . . . -176.25(17) ?
    N2 C14 C15 C20 . . . . 2.6(3) ?
    N2 C14 C15 C16 . . . . -175.16(19) ?
    C20 C15 C16 C17 . . . . -0.2(3) ?
    C14 C15 C16 C17 . . . . 177.60(19) ?
    C15 C16 C17 C18 . . . . -0.4(3) ?
    C16 C17 C18 C19 . . . . 1.1(3) ?
    C17 C18 C19 O4 . . . . 178.80(19) ?
    C17 C18 C19 C20 . . . . -1.2(3) ?
    C23 O4 C19 C18 . . . . 4.2(3) ?
    C23 O4 C19 C20 . . . . -175.79(17) ?
    C18 C19 C20 O2 . . . . -179.31(18) ?
    O4 C19 C20 O2 . . . . 0.6(2) ?
    C18 C19 C20 C15 . . . . 0.6(3) ?
    O4 C19 C20 C15 . . . . -179.42(17) ?
    C16 C15 C20 O2 . . . . -179.95(18) ?
    C14 C15 C20 O2 . . . . 2.2(3) ?
    C16 C15 C20 C19 . . . . 0.1(3) ?
    C14 C15 C20 C19 . . . . -177.71(18) ?
    C2 O3 C21 C22 . . . . -177.08(16) ?
    C19 O4 C23 C24 . . . . 177.06(17) ?
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
    O1 H1 N1 . 0.84 1.84 2.584(2) 146 y
    O1W H1W1 O2 1_655 0.86(3) 2.24(3) 2.947(2) 139(3) y
    O1W H1W1 O4 1_655 0.86(3) 2.28(3) 3.018(2) 145(3) y
    O2 H2 N2 . 0.84 1.87 2.609(2) 146 y
    O1W H2W1 O1 1_655 0.78(3) 2.30(3) 3.061(2) 166(3) y
    O1W H2W1 O3 1_655 0.78(3) 2.43(3) 2.967(2) 127(3) y
    O5 H5 O1W 4_566 0.84 1.82 2.659(3) 179 y
    C7 H7A O5 . 0.95 2.33 3.242(3) 162 y
