##############################################################################
###                                                                        ###
###        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     2010-04-03
_journal_date_accepted     2010-04-15
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      5
_journal_page_first     o1128
_journal_page_last     o1128
_journal_paper_category     QO
_journal_coeditor_code     FK2017
_publ_contact_author_name     ' Zhong-Yu Duan '
_publ_contact_author_address
;
School of Chemical Engineering , Hebei University of Technology
Tianjin 300130,People^,^s Republic of China.
;
_publ_contact_author_email     zyduan@hebut.edu.cn
_publ_contact_author_fax     86-22-60202443
_publ_contact_author_phone     86-22-60200434
_publ_section_title
;
2,5,11,14-Tetraoxa-8-azadispiro[13.4.0]nonadeca-15,17,19-triene
;
loop_
    _publ_author_name
    _publ_author_address
    "Gan, Quanying"
;
Hebei University of Technology
Tianjin 300130
People's Republic of China
;
    "Yang, Liping"
;
Hebei University of Technology
Tianjin 300130
People's Republic of China
;
    "Guo, Peng"
;
Hebei University of Technology
Tianjin 300130
People's Republic of China
;
    "Yang, Jin"
;
Hebei University of Technology
Tianjin 300130
People's Republic of China
;
    "Duan, Zhongyu"
;
Hebei University of Technology
Tianjin 300130
People's Republic of China
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2,5,11,14-Tetraoxa-8-azadispiro[13.4.0]nonadeca-15,17,19-triene
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H21 N O4'
_chemical_formula_sum     'C14 H21 N O4'
_chemical_formula_iupac     'C14 H21 N O4'
_chemical_formula_weight     267.32
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     10.771(7)
_cell_length_b     8.662(5)
_cell_length_c     15.961(10)
_cell_angle_alpha     90.00
_cell_angle_beta     105.417(11)
_cell_angle_gamma     90.00
_cell_volume     1435.6(15)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     936
_cell_measurement_theta_min     2.64
_cell_measurement_theta_max     22.37
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.237
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     576
_exptl_absorpt_coefficient_mu     0.090
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min     0.951
_exptl_absorpt_correction_T_max     0.987
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(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 APEX CCD area-detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7411
_diffrn_reflns_av_R_equivalents     0.0433
_diffrn_reflns_av_sigmaI/netI     0.0531
_diffrn_reflns_theta_min     1.32
_diffrn_reflns_theta_max     24.99
_diffrn_reflns_theta_full     24.99
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_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 >
2σ(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     2717
_reflns_number_gt     1848
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0979
_refine_ls_R_factor_gt     0.0649
_refine_ls_wR_factor_gt     0.1494
_refine_ls_wR_factor_ref     0.1750
_refine_ls_goodness_of_fit_ref     1.052
_refine_ls_restrained_S_all     1.051
_refine_ls_number_reflns     2717
_refine_ls_number_parameters     343
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1029P)²+0.0778P] 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     0.427
_refine_diff_density_min     -0.195
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
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 0.0000
                         '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 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT (Bruker, 2001)'
_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 local programs'
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
    N N1 0.3503(4) 0.5129(6) 0.1371(3) 0.0573(12) Uani d . 1 . .
    H H1 0.4359 0.5187 0.1535 0.069 Uiso d R 1 . .
    N N2 0.7083(4) 0.0166(6) 0.5069(3) 0.0595(13) Uani d . 1 . .
    H H2A 0.7519 0.0117 0.4668 0.071 Uiso d R 1 . .
    O O1 0.7230(3) 0.4836(4) 0.2096(2) 0.0488(9) Uani d . 1 . .
    O O2 0.6683(4) 0.6169(4) 0.0602(2) 0.0579(10) Uani d . 1 . .
    O O3 0.4078(4) 0.5783(5) -0.0279(2) 0.0585(11) Uani d . 1 . .
    O O4 0.5273(4) 0.3439(5) 0.2723(3) 0.0604(11) Uani d . 1 . .
    O O5 0.9938(3) 0.1199(4) 0.3925(2) 0.0545(10) Uani d . 1 . .
    O O6 0.8056(3) -0.0162(4) 0.2862(2) 0.0479(9) Uani d . 1 . .
    O O7 0.6115(4) -0.1540(5) 0.3498(3) 0.0637(11) Uani d . 1 . .
    O O8 0.9812(4) 0.0834(5) 0.5652(3) 0.0596(11) Uani d . 1 . .
    C C1 0.8137(5) 0.4670(6) 0.1632(3) 0.0488(13) Uani d . 1 . .
    C C2 0.9266(5) 0.3848(7) 0.1912(4) 0.0650(18) Uani d . 1 . .
    H H2 0.9467 0.3381 0.2457 0.078 Uiso calc R 1 . .
    C C3 1.0097(6) 0.3708(11) 0.1397(6) 0.091(3) Uani d . 1 . .
    H H3 1.0850 0.3136 0.1586 0.109 Uiso calc R 1 . .
    C C4 0.9809(6) 0.4413(12) 0.0610(6) 0.091(3) Uani d . 1 . .
    H H4 1.0376 0.4315 0.0265 0.109 Uiso calc R 1 . .
    C C5 0.8682(6) 0.5286(8) 0.0300(4) 0.0700(18) Uani d . 1 . .
    H H5 0.8513 0.5778 -0.0236 0.084 Uiso calc R 1 . .
    C C6 0.7824(5) 0.5399(6) 0.0812(3) 0.0480(13) Uani d . 1 . .
    C C7 0.6160(6) 0.6595(8) -0.0305(4) 0.0656(17) Uani d . 1 . .
    H H7A 0.6173 0.5720 -0.0681 0.079 Uiso calc R 1 . .
    H H7B 0.6656 0.7429 -0.0462 0.079 Uiso calc R 1 . .
    C C8 0.4788(6) 0.7108(7) -0.0382(4) 0.0621(17) Uani d . 1 . .
    H H8A 0.4770 0.7864 0.0063 0.075 Uiso calc R 1 . .
    H H8B 0.4420 0.7573 -0.0947 0.075 Uiso calc R 1 . .
    C C9 0.2861(5) 0.6140(8) -0.0110(4) 0.0655(17) Uani d . 1 . .
    H H9A 0.2277 0.5281 -0.0299 0.079 Uiso calc R 1 . .
    H H9B 0.2492 0.7037 -0.0450 0.079 Uiso calc R 1 . .
    C C10 0.2971(6) 0.6457(8) 0.0824(4) 0.0623(16) Uani d . 1 . .
    H H10A 0.3523 0.7346 0.1009 0.075 Uiso calc R 1 . .
    H H10B 0.2127 0.6701 0.0896 0.075 Uiso calc R 1 . .
    C C11 0.3550(6) 0.5332(8) 0.2280(4) 0.0634(16) Uani d . 1 . .
    H H11A 0.2695 0.5575 0.2333 0.076 Uiso calc R 1 . .
    H H11B 0.4113 0.6190 0.2516 0.076 Uiso calc R 1 . .
    C C12 0.4036(6) 0.3892(8) 0.2795(4) 0.0719(18) Uani d . 1 . .
    H H12A 0.4080 0.4073 0.3401 0.086 Uiso calc R 1 . .
    H H12B 0.3431 0.3058 0.2590 0.086 Uiso calc R 1 . .
    C C13 0.6295(6) 0.4306(8) 0.3246(4) 0.0628(16) Uani d . 1 . .
    H H13A 0.6468 0.3978 0.3848 0.075 Uiso calc R 1 . .
    H H13B 0.6074 0.5394 0.3214 0.075 Uiso calc R 1 . .
    C C14 0.7460(6) 0.4043(7) 0.2915(4) 0.0636(17) Uani d . 1 . .
    H H14A 0.8225 0.4449 0.3323 0.076 Uiso calc R 1 . .
    H H14B 0.7583 0.2949 0.2838 0.076 Uiso calc R 1 . .
    C C15 1.0249(5) 0.0476(6) 0.3258(3) 0.0465(13) Uani d . 1 . .
    C C16 1.1469(6) 0.0433(9) 0.3128(5) 0.0717(18) Uani d . 1 . .
    H H16 1.2155 0.0918 0.3517 0.086 Uiso calc R 1 . .
    C C17 1.1656(7) -0.0350(12) 0.2405(5) 0.093(3) Uani d . 1 . .
    H H17 1.2469 -0.0365 0.2306 0.111 Uiso calc R 1 . .
    C C18 1.0679(9) -0.1073(10) 0.1856(5) 0.092(3) Uani d . 1 . .
    H H18 1.0827 -0.1593 0.1383 0.111 Uiso calc R 1 . .
    C C19 0.9450(6) -0.1071(8) 0.1971(4) 0.0664(18) Uani d . 1 . .
    H H19 0.8787 -0.1600 0.1586 0.080 Uiso calc R 1 . .
    C C20 0.9218(5) -0.0267(6) 0.2672(3) 0.0490(13) Uani d . 1 . .
    C C21 0.6986(6) -0.0989(7) 0.2322(4) 0.0611(17) Uani d . 1 . .
    H H21A 0.7184 -0.2081 0.2316 0.073 Uiso calc R 1 . .
    H H21B 0.6784 -0.0604 0.1730 0.073 Uiso calc R 1 . .
    C C22 0.5881(5) -0.0732(8) 0.2704(4) 0.0624(16) Uani d . 1 . .
    H H22A 0.5787 0.0362 0.2803 0.075 Uiso calc R 1 . .
    H H22B 0.5090 -0.1099 0.2307 0.075 Uiso calc R 1 . .
    C C23 0.5317(6) -0.1077(9) 0.4040(5) 0.0733(19) Uani d . 1 . .
    H H23A 0.5265 -0.1918 0.4430 0.088 Uiso calc R 1 . .
    H H23B 0.4454 -0.0881 0.3677 0.088 Uiso calc R 1 . .
    C C24 0.5793(5) 0.0330(9) 0.4564(4) 0.0691(18) Uani d . 1 . .
    H H24A 0.5735 0.1207 0.4178 0.083 Uiso calc R 1 . .
    H H24B 0.5247 0.0537 0.4946 0.083 Uiso calc R 1 . .
    C C25 0.7610(6) 0.1461(8) 0.5623(4) 0.0652(17) Uani d . 1 . .
    H H25A 0.7063 0.1674 0.6004 0.078 Uiso calc R 1 . .
    H H25B 0.7604 0.2366 0.5265 0.078 Uiso calc R 1 . .
    C C26 0.8935(6) 0.1184(9) 0.6157(4) 0.0680(17) Uani d . 1 . .
    H H26A 0.9238 0.2094 0.6505 0.082 Uiso calc R 1 . .
    H H26B 0.8928 0.0333 0.6551 0.082 Uiso calc R 1 . .
    C C27 1.0351(6) 0.2157(7) 0.5353(4) 0.0598(16) Uani d . 1 . .
    H H27A 1.0986 0.2630 0.5831 0.072 Uiso calc R 1 . .
    H H27B 0.9681 0.2909 0.5120 0.072 Uiso calc R 1 . .
    C C28 1.0969(5) 0.1666(8) 0.4664(4) 0.0623(16) Uani d . 1 . .
    H H28A 1.1451 0.2515 0.4507 0.075 Uiso calc R 1 . .
    H H28B 1.1554 0.0812 0.4867 0.075 Uiso calc R 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
    N1 C11 . 1.450(7) ?
    N1 C10 . 1.465(8) ?
    N1 H1 . 0.8900 ?
    N2 C24 . 1.416(7) ?
    N2 C25 . 1.448(8) ?
    N2 H2A . 0.8900 ?
    O1 C1 . 1.382(6) ?
    O1 C14 . 1.439(7) ?
    O2 C6 . 1.360(6) ?
    O2 C7 . 1.454(7) ?
    O3 C8 . 1.413(7) ?
    O3 C9 . 1.440(7) ?
    O4 C13 . 1.409(7) ?
    O4 C12 . 1.422(8) ?
    O5 C15 . 1.352(6) ?
    O5 C28 . 1.446(6) ?
    O6 C20 . 1.367(6) ?
    O6 C21 . 1.434(6) ?
    O7 C22 . 1.410(7) ?
    O7 C23 . 1.429(8) ?
    O8 C27 . 1.423(8) ?
    O8 C26 . 1.428(7) ?
    C1 C2 . 1.377(8) ?
    C1 C6 . 1.412(8) ?
    C2 C3 . 1.372(10) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.357(11) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.403(10) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.390(8) ?
    C5 H5 . 0.9300 ?
    C7 C8 . 1.516(9) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 C10 . 1.489(9) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 C12 . 1.508(10) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 C14 . 1.503(9) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C15 C16 . 1.384(8) ?
    C15 C20 . 1.403(7) ?
    C16 C17 . 1.398(11) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.333(11) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.383(10) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.395(8) ?
    C19 H19 . 0.9300 ?
    C21 C22 . 1.492(9) ?
    C21 H21A . 0.9700 ?
    C21 H21B . 0.9700 ?
    C22 H22A . 0.9700 ?
    C22 H22B . 0.9700 ?
    C23 C24 . 1.490(10) ?
    C23 H23A . 0.9700 ?
    C23 H23B . 0.9700 ?
    C24 H24A . 0.9700 ?
    C24 H24B . 0.9700 ?
    C25 C26 . 1.474(8) ?
    C25 H25A . 0.9700 ?
    C25 H25B . 0.9700 ?
    C26 H26A . 0.9700 ?
    C26 H26B . 0.9700 ?
    C27 C28 . 1.490(8) ?
    C27 H27A . 0.9700 ?
    C27 H27B . 0.9700 ?
    C28 H28A . 0.9700 ?
    C28 H28B . 0.9700 ?
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
    C11 N1 C10 . . 113.9(5) ?
    C11 N1 H1 . . 86.5 ?
    C10 N1 H1 . . 110.0 ?
    C24 N2 C25 . . 115.8(5) ?
    C24 N2 H2A . . 102.8 ?
    C25 N2 H2A . . 106.3 ?
    C1 O1 C14 . . 117.5(4) ?
    C6 O2 C7 . . 117.0(4) ?
    C8 O3 C9 . . 113.3(5) ?
    C13 O4 C12 . . 114.0(5) ?
    C15 O5 C28 . . 118.4(4) ?
    C20 O6 C21 . . 118.0(4) ?
    C22 O7 C23 . . 114.3(5) ?
    C27 O8 C26 . . 114.1(5) ?
    C2 C1 O1 . . 124.7(5) ?
    C2 C1 C6 . . 120.3(5) ?
    O1 C1 C6 . . 115.0(4) ?
    C3 C2 C1 . . 120.7(7) ?
    C3 C2 H2 . . 119.6 ?
    C1 C2 H2 . . 119.6 ?
    C4 C3 C2 . . 119.3(7) ?
    C4 C3 H3 . . 120.3 ?
    C2 C3 H3 . . 120.3 ?
    C3 C4 C5 . . 122.2(7) ?
    C3 C4 H4 . . 118.9 ?
    C5 C4 H4 . . 118.9 ?
    C6 C5 C4 . . 118.6(7) ?
    C6 C5 H5 . . 120.7 ?
    C4 C5 H5 . . 120.7 ?
    O2 C6 C5 . . 126.1(5) ?
    O2 C6 C1 . . 115.1(4) ?
    C5 C6 C1 . . 118.8(5) ?
    O2 C7 C8 . . 105.5(5) ?
    O2 C7 H7A . . 110.6 ?
    C8 C7 H7A . . 110.6 ?
    O2 C7 H7B . . 110.6 ?
    C8 C7 H7B . . 110.6 ?
    H7A C7 H7B . . 108.8 ?
    O3 C8 C7 . . 107.3(5) ?
    O3 C8 H8A . . 110.2 ?
    C7 C8 H8A . . 110.2 ?
    O3 C8 H8B . . 110.2 ?
    C7 C8 H8B . . 110.2 ?
    H8A C8 H8B . . 108.5 ?
    O3 C9 C10 . . 113.1(5) ?
    O3 C9 H9A . . 109.0 ?
    C10 C9 H9A . . 109.0 ?
    O3 C9 H9B . . 109.0 ?
    C10 C9 H9B . . 109.0 ?
    H9A C9 H9B . . 107.8 ?
    N1 C10 C9 . . 111.5(5) ?
    N1 C10 H10A . . 109.3 ?
    C9 C10 H10A . . 109.3 ?
    N1 C10 H10B . . 109.3 ?
    C9 C10 H10B . . 109.3 ?
    H10A C10 H10B . . 108.0 ?
    N1 C11 C12 . . 111.1(5) ?
    N1 C11 H11A . . 109.4 ?
    C12 C11 H11A . . 109.4 ?
    N1 C11 H11B . . 109.4 ?
    C12 C11 H11B . . 109.4 ?
    H11A C11 H11B . . 108.0 ?
    O4 C12 C11 . . 112.4(5) ?
    O4 C12 H12A . . 109.1 ?
    C11 C12 H12A . . 109.1 ?
    O4 C12 H12B . . 109.1 ?
    C11 C12 H12B . . 109.1 ?
    H12A C12 H12B . . 107.8 ?
    O4 C13 C14 . . 107.7(5) ?
    O4 C13 H13A . . 110.2 ?
    C14 C13 H13A . . 110.2 ?
    O4 C13 H13B . . 110.2 ?
    C14 C13 H13B . . 110.2 ?
    H13A C13 H13B . . 108.5 ?
    O1 C14 C13 . . 106.8(4) ?
    O1 C14 H14A . . 110.4 ?
    C13 C14 H14A . . 110.4 ?
    O1 C14 H14B . . 110.4 ?
    C13 C14 H14B . . 110.4 ?
    H14A C14 H14B . . 108.6 ?
    O5 C15 C16 . . 125.0(5) ?
    O5 C15 C20 . . 114.8(4) ?
    C16 C15 C20 . . 120.1(6) ?
    C15 C16 C17 . . 119.2(7) ?
    C15 C16 H16 . . 120.4 ?
    C17 C16 H16 . . 120.4 ?
    C18 C17 C16 . . 120.5(6) ?
    C18 C17 H17 . . 119.7 ?
    C16 C17 H17 . . 119.7 ?
    C17 C18 C19 . . 121.9(7) ?
    C17 C18 H18 . . 119.0 ?
    C19 C18 H18 . . 119.0 ?
    C18 C19 C20 . . 119.2(7) ?
    C18 C19 H19 . . 120.4 ?
    C20 C19 H19 . . 120.4 ?
    O6 C20 C19 . . 125.5(5) ?
    O6 C20 C15 . . 115.5(4) ?
    C19 C20 C15 . . 119.0(5) ?
    O6 C21 C22 . . 106.3(5) ?
    O6 C21 H21A . . 110.5 ?
    C22 C21 H21A . . 110.5 ?
    O6 C21 H21B . . 110.5 ?
    C22 C21 H21B . . 110.5 ?
    H21A C21 H21B . . 108.7 ?
    O7 C22 C21 . . 108.8(5) ?
    O7 C22 H22A . . 109.9 ?
    C21 C22 H22A . . 109.9 ?
    O7 C22 H22B . . 109.9 ?
    C21 C22 H22B . . 109.9 ?
    H22A C22 H22B . . 108.3 ?
    O7 C23 C24 . . 113.4(5) ?
    O7 C23 H23A . . 108.9 ?
    C24 C23 H23A . . 108.9 ?
    O7 C23 H23B . . 108.9 ?
    C24 C23 H23B . . 108.9 ?
    H23A C23 H23B . . 107.7 ?
    N2 C24 C23 . . 112.1(5) ?
    N2 C24 H24A . . 109.2 ?
    C23 C24 H24A . . 109.2 ?
    N2 C24 H24B . . 109.2 ?
    C23 C24 H24B . . 109.2 ?
    H24A C24 H24B . . 107.9 ?
    N2 C25 C26 . . 112.9(5) ?
    N2 C25 H25A . . 109.0 ?
    C26 C25 H25A . . 109.0 ?
    N2 C25 H25B . . 109.0 ?
    C26 C25 H25B . . 109.0 ?
    H25A C25 H25B . . 107.8 ?
    O8 C26 C25 . . 113.1(5) ?
    O8 C26 H26A . . 109.0 ?
    C25 C26 H26A . . 109.0 ?
    O8 C26 H26B . . 109.0 ?
    C25 C26 H26B . . 109.0 ?
    H26A C26 H26B . . 107.8 ?
    O8 C27 C28 . . 108.7(5) ?
    O8 C27 H27A . . 110.0 ?
    C28 C27 H27A . . 110.0 ?
    O8 C27 H27B . . 110.0 ?
    C28 C27 H27B . . 110.0 ?
    H27A C27 H27B . . 108.3 ?
    O5 C28 C27 . . 106.5(4) ?
    O5 C28 H28A . . 110.4 ?
    C27 C28 H28A . . 110.4 ?
    O5 C28 H28B . . 110.4 ?
    C27 C28 H28B . . 110.4 ?
    H28A C28 H28B . . 108.6 ?
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
    C14 O1 C1 C2 . . . . -2.5(7) ?
    C14 O1 C1 C6 . . . . 176.5(4) ?
    O1 C1 C2 C3 . . . . 178.2(6) ?
    C6 C1 C2 C3 . . . . -0.7(9) ?
    C1 C2 C3 C4 . . . . 1.1(11) ?
    C2 C3 C4 C5 . . . . -0.1(12) ?
    C3 C4 C5 C6 . . . . -1.4(11) ?
    C7 O2 C6 C5 . . . . 15.7(8) ?
    C7 O2 C6 C1 . . . . -164.7(5) ?
    C4 C5 C6 O2 . . . . -178.6(6) ?
    C4 C5 C6 C1 . . . . 1.8(8) ?
    C2 C1 C6 O2 . . . . 179.6(5) ?
    O1 C1 C6 O2 . . . . 0.6(6) ?
    C2 C1 C6 C5 . . . . -0.8(7) ?
    O1 C1 C6 C5 . . . . -179.8(5) ?
    C6 O2 C7 C8 . . . . 168.2(5) ?
    C9 O3 C8 C7 . . . . 164.6(4) ?
    O2 C7 C8 O3 . . . . -69.4(6) ?
    C8 O3 C9 C10 . . . . -83.9(7) ?
    C11 N1 C10 C9 . . . . -176.0(5) ?
    O3 C9 C10 N1 . . . . -59.7(7) ?
    C10 N1 C11 C12 . . . . 176.8(5) ?
    C13 O4 C12 C11 . . . . 78.4(6) ?
    N1 C11 C12 O4 . . . . 57.2(7) ?
    C12 O4 C13 C14 . . . . -163.3(5) ?
    C1 O1 C14 C13 . . . . -175.5(5) ?
    O4 C13 C14 O1 . . . . 71.4(6) ?
    C28 O5 C15 C16 . . . . -14.8(8) ?
    C28 O5 C15 C20 . . . . 165.2(5) ?
    O5 C15 C16 C17 . . . . -179.5(6) ?
    C20 C15 C16 C17 . . . . 0.4(9) ?
    C15 C16 C17 C18 . . . . -1.4(11) ?
    C16 C17 C18 C19 . . . . 0.6(13) ?
    C17 C18 C19 C20 . . . . 1.2(11) ?
    C21 O6 C20 C19 . . . . 2.5(8) ?
    C21 O6 C20 C15 . . . . -175.7(4) ?
    C18 C19 C20 O6 . . . . 179.8(6) ?
    C18 C19 C20 C15 . . . . -2.1(9) ?
    O5 C15 C20 O6 . . . . -0.4(6) ?
    C16 C15 C20 O6 . . . . 179.6(5) ?
    O5 C15 C20 C19 . . . . -178.7(5) ?
    C16 C15 C20 C19 . . . . 1.3(8) ?
    C20 O6 C21 C22 . . . . 177.2(5) ?
    C23 O7 C22 C21 . . . . 164.3(5) ?
    O6 C21 C22 O7 . . . . -70.3(6) ?
    C22 O7 C23 C24 . . . . -82.3(6) ?
    C25 N2 C24 C23 . . . . -177.9(5) ?
    O7 C23 C24 N2 . . . . -54.7(8) ?
    C24 N2 C25 C26 . . . . 177.5(5) ?
    C27 O8 C26 C25 . . . . 85.5(7) ?
    N2 C25 C26 O8 . . . . 57.8(8) ?
    C26 O8 C27 C28 . . . . -165.8(4) ?
    C15 O5 C28 C27 . . . . -169.9(5) ?
    O8 C27 C28 O5 . . . . 68.3(6) ?
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
    C21 H21B O3 2_645 0.97 2.56 3.511(2) 168 yes
    C26 H26A Cg1 . 0.97 2.69 3.646(2) 168 yes
